Analytical Chiral SFC · 2014. 10. 29. · Introduction In the 1960s, University of Utah Professor...

Analytical Chiral SFC

Application Guide 1

Introduction

In the 1960s, University of Utah Professor J. CalvinGiddings discovered the phenomenon of supercritical fluid chromatography (SFC).

Nearly 20 years later, Suprex, Inc., unveiled the first commercialized SFCanalytical instrument with great fanfare. Initially, the technique did notcatch on. Now in the 21st Century, pharmaceutical companies realize thetremendous time and cost savings of SFC chiral separations. SFC is becoming avery accepted technique for analytical through preparative separations.

Papers presented at international symposia such as SPICA, CPhI, Prep, ACS,EAS, and Pittcon, show that SFC separations are faster, show better resolution,and use less solvent than conventional methods. Furthermore, CO2 is a ‘green’solvent and is not flammable or hazardous.

Super and sub-critical CO2 modified with MeOH and other solventsoutperforms normal-phase HPLC because the flow rates are typically five timesfaster without losing resolution. This speed advantage is due to unique CO2characteristics such as low viscosity, high diffusivity and low surface tension.

SFC is an ideal preparative chromatography technique due to the vaporizationof the CO2 at the end of the preparative process, which reduces solvent removalcosts. Thus, when using preparative SFC, the chemist actually requires far lessequipment, columns, and post-chromatographic facilities meaning that thecapital and operating costs are far lower.

We hope you enjoy this sampling of applications on the Thar SFC MethodStation® using Regis Technologies columns.

Index of Compounds

Abscisic Acid ....................................... 3Acenaphthenol.................................... 31-Acetoxychavicol-Acetate ................. 3Althiazide ............................................ 39-Anthryl-Trifluoromethyl

Carbinol ......................................... 31,1’-Bi-2-Naphthol ............................. 3Bendroflumethiazide.......................... 4ß-Blocker............................................. 4Bupivacaine......................................... 4Carprofen............................................ 4Chlorflurecol Methyl Ester................. 4Chlormezanone .................................. 42-Chloromandelic Acid...................... 54-Chloromandelic Acid...................... 5Coumachlor ........................................ 5Cromakalim ........................................ 5Devrinol .............................................. 5Diclofop Methyl.................................. 5Diperodon........................................... 6Ethotoin .............................................. 6Etodolac .............................................. 6Fenoprofen.......................................... 6Flurbiprofen........................................ 6Hydrobenzoin ..................................... 6Ibuprofen ............................................ 7Ifenprodil ............................................ 7Indapamide......................................... 7Indoprofen .......................................... 7Ketoprofen .......................................... 7Ketorolac ............................................. 7ß-Lactam............................................. 8Lansoprazole ....................................... 8Leptophos ........................................... 8Loxoprofen.......................................... 8Luciferin.............................................. 8Mandelic Acid..................................... 8Metalaxyl............................................. 9

Methadone .......................................... 9α-Methoxyphenyl-Acetic Acid........... 9Metolazone.......................................... 9Modafinil ............................................ 9Mosapride ........................................... 9Nadifloxacin...................................... 10Nadolol.............................................. 10Naproxen........................................... 10Nimodipine....................................... 10Omeprazole....................................... 10Permethrin........................................ 10Phosphine Oxides............................. 11Phosphine Selenium-Oxide ............. 11Pindolol............................................. 11Proglumide ....................................... 11Propranolol ....................................... 12Resmethrin........................................ 12trans-Stilbene Oxide......................... 12Sulfinpyrazone.................................. 12Sulfoxides..................................... 12-13Sulindac............................................. 13Suprofen............................................ 13Temazepam ....................................... 13Tetrahydrobenzo(a)-pyrene-7-ol..... 13Tetrahydropalmatine ........................ 14Tetramethrin..................................... 14Tetramisole........................................ 14Thalidomide...................................... 144-(Trifluoromethyl)

-Mandelic Acid ............................ 14α-Trityl-2-Naphthalene

Propionic Acid.............................. 14Troger’s Base ..................................... 15Trolox ................................................ 15Tropicamide ...................................... 15Vanilmandelic Acid .......................... 15Warfarin ........................................... 15Zopiclone .......................................... 15

Abscisic Acid

1-Acetoxychavicol Acetate

Acenaphthenol

Althiazide

1,1’-Bi-2-Naphthol9-Anthryl Trifluoromethyl Carbinol

3 SFC Chiral Application Guide I • www.registech.com/chiral

Bendroflumethiazide

SFC Chiral Application Guide I • www.registech.com/chiral 4

Carprofen

ChlormezanoneChlorflurecol Methyl Ester

Bupivicaine

Beta-Blocker

4-Chloromandelic Acid

Cromakalim

Diclofop MethylDevrinol, (Napropamide)

Coumachlor


2-Chloromandelic Acid

Diperodon Ethotoin

Fenoprofen

HydrobenzoinFlurbiprofen

Etodolac



Ifenprodil

Indapamide Indoprofen

KetorolacKetoprofen

Ibuprofen


LansoprazoleBeta-Lactam

Leptophos

Mandelic AcidLuciferin

Loxoprofen

Metolazone

Modafinil Mosapride


α-Methoxyphenyl Acetic Acid

MethadoneMetalaxyl

Nadifloxacin Nadolol

Nimodipine

cis,trans-PermethrinOmeprazole

Naproxen



ProglumidePindolol

Phosphine Oxide #3 Phosphine Selenium Oxide

Phosphine Oxide #2Phosphine Oxide #1

Resmethrin

trans-Stilbene Oxide Sulfinpyrazone


Sulfoxide #1 Sulfoxide #2

Propranolol


Tetrahydrobenzo(a)pyrene-7-ol

Sulfoxide #4Sulfoxide #3

Temazepam

SuprofenSulindac


Tetrahydropalmatine Tetramethrin

Tetramisole Thalidomide

α-Trityl-2-Naphthalene Propionic Acid4-Trifluoromethyl Mandelic Acid


Troger’s Base Trolox

Tropicamide Vanilmandelic Acid

Warfarin Zopiclone

Regis HPLC Chiral Column Product List PRODUCT PARTICLE SIZE COLUMN DIMENSIONS PRODUCT# ---------------------------------------------------------------------------------------------------------------------------------(R,R)-Whelk-O 1 5 µm, 100 Å 25 cm x 4.6 mm 786201 (R,R)-Whelk-O 1 5 µm, 100 Å 25 cm x 10.0 mm 786202 (R,R)-Whelk-O 1 5 µm, 100 Å 25 cm x 30.0 mm 786205 (S,S)-Whelk-O 1 5 µm, 100 Å 25 cm x 4.6 mm 786101 (S,S)-Whelk-O 1 5 µm, 100 Å 25 cm x 10.0 mm 786102 (S,S)-Whelk-O 1 5 µm, 100 Å 25 cm x 30.0 mm 786105 --------------------------------------------------------------------------------------------------------------------------------- (R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 4.6 mm 786515 (R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 10.0 mm 786525 (R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 21.1 mm 786535 (R,R)-Whelk-O 1 10 µm, 100 Å 50 cm x 21.1 mm 786545 (R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 30.0 mm 786708 (R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 50.0 mm 786709 (R,R)-Whelk-O 1 10 µm, 100 Å 50 cm x 30.0 mm 786713 (R,R)-Whelk-O 1 10 µm, 100 Å 50 cm x 50.0 mm 786710 (S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 4.6 mm 786615 (S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 10.0 mm 786625 (S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 21.1mm 786635 (S,S)-Whelk-O 1 10 µm, 100 Å 50 cm x 21.1 mm 786645 (S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 30.0 mm 786702 (S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 50.0 mm 786703 (S,S)-Whelk-O 1 10 µm, 100 Å 50 cm x 30.0 mm 786716 (S,S)-Whelk-O 1 10 µm, 100 Å 50 cm x 50.0 mm 786704 --------------------------------------------------------------------------------------------------------------------------------- (R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 4.6 mm 786315 (R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 10.0 mm 786325 (R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 21.1 mm 786335 (R,R)-Whelk-O 2 10 µm, 100 Å 50 cm x 21.1 mm 786345 (R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 30.0 mm 786727 (R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 50.0 mm 786728 (R,R)-Whelk-O 2 10 µm, 100 Å 50 cm x 30.0 mm 786732 (R,R)-Whelk-O 2 10 µm, 100 Å 50 cm x 50.0 mm 786729 (S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 4.6 mm 786415 (S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 10.0 mm 786425 (S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 21.1mm 786435 (S,S)-Whelk-O 2 10 µm, 100 Å 50 cm x 21.1 mm 786445 (S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 30.0 mm 786721 (S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 50.0 mm 786722 (S,S)-Whelk-O 2 10 µm, 100 Å 50 cm x 30.0 mm 786736 (S,S)-Whelk-O 2 10 µm, 100 Å 50 cm x 50.0 mm 786723 --------------------------------------------------------------------------------------------------------------------------------- (R,R)-ULMO 5 µm, 100 Å 25 cm x 4.6 mm 787200 (R,R)-ULMO 5 µm, 100 Å 25 cm x 10.0 mm 787201 (R,R)-ULMO 5 µm, 100 Å 25 cm x 30.0 mm 787203 (S,S)-ULMO 5 µm, 100 Å 25 cm x 4.6 mm 787100 (S,S)-ULMO 5 µm, 100 Å 25 cm x 10.0 mm 787101 (S,S)-ULMO 5 µm, 100 Å 25 cm x 30.0 mm 787103 --------------------------------------------------------------------------------------------------------------------------------- (R,R)-ULMO 10 µm, 100 Å 25 cm x 21.1 mm 787202 (R,R)-ULMO 10 µm, 100 Å 25 cm x 30.0 mm 787707 (R,R)-ULMO 10 µm, 100 Å 25 cm x 50.0 mm 787708 (R,R)-ULMO 10 µm, 100 Å 50 cm x 30.0 mm 787712 (R,R)-ULMO 10 µm, 100 Å 50 cm x 50.0 mm 787709 (S,S)-ULMO 10 µm, 100 Å 25 cm x 21.1 mm 787102 (S,S)-ULMO 10 µm, 100 Å 25 cm x 30.0 mm 787701 SFC Chiral Application Guide I • www.registech.com/chiral 16

Regis HPLC Chiral Column Product List (S,S)-ULMO 10 µm, 100 Å 25 cm x 50.0 mm 787702 (S,S)-ULMO 10 µm, 100 Å 50 cm x 30.0 mm 787715 (S,S)-ULMO 10 µm, 100 Å 50 cm x 50.0 mm 787703 --------------------------------------------------------------------------------------------------------------------------------- (R,R)-DACH-DNB 5 µm, 100 Å 25 cm x 4.6 mm 788101 (R,R)-DACH-DNB 5 µm, 100 Å 25 cm x 10.0 mm 788102 (R,R)-DACH-DNB 5 µm, 100 Å 25 cm x 30.0 mm 788104 (S,S)-DACH-DNB 5 µm, 100 Å 25 cm x 4.6 mm 788201 (S,S)-DACH-DNB 5 µm, 100 Å 25 cm x 10.0 mm 788202 (S,S)-DACH-DNB 5 µm, 100 Å 25 cm x 30.0 mm 788204 --------------------------------------------------------------------------------------------------------------------------------- (R,R)-DACH-DNB 10 µm, 100 Å 25 cm x 21.1 mm 788103 (R,R)-DACH-DNB 10 µm, 100 Å 25 cm x 30.0 mm 788707 (R,R)-DACH-DNB 10 µm, 100 Å 25 cm x 50.0 mm 788708 (R,R)-DACH-DNB 10 µm, 100 Å 50 cm x 30.0 mm 788712 (R,R)-DACH-DNB 10 µm, 100 Å 50 cm x 50.0 mm 788709 (S,S)-DACH-DNB 10 µm, 100 Å 25 cm x 21.1 mm 788203 (S,S)-DACH-DNB 10 µm, 100 Å 25 cm x 30.0 mm 788701 (S,S)-DACH-DNB 10 µm, 100 Å 25 cm x 50.0 mm 788702 (S,S)-DACH-DNB 10 µm, 100 Å 50 cm x 30.0 mm 788715 (S,S)-DACH-DNB 10 µm, 100 Å 50 cm x 50.0 mm 788705 --------------------------------------------------------------------------------------------------------------------------------- (3R,4S)-Pirkle 1-J 5 µm, 100 Å 25 cm x 4.6 mm 731044 (3R,4S)-Pirkle 1-J 5 µm, 100 Å 25 cm x 10.0 mm 731244 (3S,4R)-Pirkle 1-J 5 µm, 100 Å 25 cm x 4.6 mm 731045 (3S,4R)-Pirkle 1-J 5 µm, 100 Å 25 cm x 10.0 mm 731245 --------------------------------------------------------------------------------------------------------------------------------- (R,R)-α-Burke 2 5 µm, 100 Å 25 cm x 4.6 mm 735035 (R,R)-α-Burke 2 5 µm, 100 Å 25 cm x 10.0 mm 735235 (S,S)-α-Burke 2 5 µm, 100 Å 25 cm x 4.6 mm 735037 (S,S)-α-Burke 2 5 µm, 100 Å 25 cm x 10.0 mm 735237 --------------------------------------------------------------------------------------------------------------------------------- (R,R)-β-Gem 1 5 µm, 100 Å 25 cm x 4.6 mm 731043 (R,R)-β-Gem 1 5 µm, 100 Å 25 cm x 10.0 mm 731243 (S,S)-β-Gem 1 5 µm, 100 Å 25 cm x 4.6 mm 731029 (S,S)-β-Gem 1 5 µm, 100 Å 25 cm x 10.0 mm 731229 --------------------------------------------------------------------------------------------------------------------------------- D-Leucine 5 µm, 100 Å 25 cm x 4.6 mm 731054 D-Leucine 5 µm, 100 Å 25 cm x 10.0 mm 731254 L-Leucine 5 µm, 100 Å 25 cm x 4.6 mm 731041 L-Leucine 5 µm, 100 Å 25 cm x 10.0 mm 731241 ---------------------------------------------------------------------------------------------------------------------------------D-Phenylglycine 5 µm, 100 Å 25 cm x 4.6 mm 731021 D-Phenylglycine 5 µm, 100 Å 25 cm x 10.0 mm 731221 L-Phenylglycine 5 µm, 100 Å 25 cm x 4.6 mm 731024 L-Phenylglycine 5 µm, 100 Å 25 cm x 10.0 mm 731224 --------------------------------------------------------------------------------------------------------------------------------- L-Naphthylleucine 5 µm, 100 Å 25 cm x 4.6 mm 731034 L-Naphthylleucine 5 µm, 100 Å 25 cm x 10.0mm 731234

● Bulk material is available for all Chiral Stationary Phases ● For column dimensions not listed, please contact Regis 17 SFC Chiral Application Guide I • www.registech.com/chiral


Free Chiral Screening on HPLC and SFC

Mr. Francis Mannerino Ted SzczerbaDirector of Chromatography Division Technical DirectorPhone: 847-583-7662 Phone: 847-583-7661Fax: 847-967-1214 Fax: 847-967-1214e-mail: [email protected] e-mail: [email protected]

Ms. Jelena Kocergin Andy MilesInternational Sales Manager Chiral Sales SpecialistPhone: 847-583-7649 Phone: 317-919-7947Fax: 847-967-1214 Fax: 847-967-1214 e-mail: [email protected] e-mail: [email protected]

Sean F. Bradley Hamilton LenoxDirector of Business Development Manager of Sales Central RegionPhone: 847-583-7631 Phone: 773-354-1330Fax: 847-967-1214 Fax: 847-967-1214e-mail: [email protected] e-mail: [email protected]

Elena Chekhova, Ph.D. Deb Minor, Ph.D.Manager of Sales Eastern Region Sales RepresentativePhone: 617-669-4661 Phone: 919-602-2167Fax: 847-967-1214 Fax: 847-967-1214e-mail: [email protected] email: [email protected]

Since the introduction of the first Pirkle Type Chiral HPLC column in 1980, RegisTechnologies has been a recognized leadingmanufacturer of chiral stationary phases. TheRegis team is dedicated to providing the besttechnical support as well as outstanding methoddevelopment support for the resolution of chiralcompounds.

At Regis, we embrace new advances in separationtechnology. We recently installed an analyticalSFC unit since we feel SFC is a promisingtechnique. Regis now offers Free Chiral Screening

in both HPLC and SFC. Our goal is to give youthe best resolution method for your compound by identifying the best Pirkle-type column andseparation technique based on your needs.

This new SFC guide contains only a sample of thecompounds separated on our columns using aThar Method Station® SFC. New methods aredeveloped each month.

For sales inquires, technical assistance and FreeChiral Screening information, please contact aRegis team member listed below:

Regis Technologies,Inc8210 Austin Ave.Morton Grove, IL 60053

For Sales and Technical assistance:Phone: 847-967-6000

Fax: [email protected]

www.registech.com/chiral

IntroductionIndex of CompoundsPage 3Page 4Page 5Page 6Page 7Page 8Page 9Page 10Page 11Page 12Page 13Page 14Page 15Product ListProduct List Cont.Free Screening InfoContact Info

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