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‘Green’ Architects
‘Green’ Builders
Southeast Asia’s first ‘zero’ energy buildingBradell Road, Singapore
Floor Diffusers
Dimmers/Sensors
Fluorescent Lighting
PhotovoltaicsSolar Chimney
Shading Devices
The Historical ‘Toolkit’
Capability = Tools & Methods + People
The Tools & Methods NeededThe Tools & Methods Needed
• Sustainable Manufacturing Problem Areas– Chemical Transformations– Biotransformations– Physical Transformations– Solvent Selection and Optimization– Unit Operation Selection and Optimization– Equipment and Technology Selection– Controls Selection and Optimization– Recovery and Reuse Integration– Waste Treatment and Minimization– Lifecycle Analysis– Facilities and Supply Chain
1st RFP, 27 Jan 10
J. Am. Chem. Soc., 2003, 125 (28), pp 8456–8457
R1+
R2
Pd-catalyst
LigandOxidantSolvent
R1
R2
A/Prof Robin Chi, NTU“New Green Organocatalytic Methods for Atom-Economic Amide Synthesis”
Dr Rudiyanto Gunawan, NUS“Single-step crystallisation in droplets for sustainable drug formulation processes”
A/Prof. Reginald Tan, ICES & NUS“Enhanced Bioavailability through formulating amorphous forms with porous biocompatible excipients”
A/Prof. Loh Kai Chee, NUS“Enhanced and sustainable biohydroxylation reactions for pharmaceutical production”
Dr. Anqi Chen (ICES) “Development of cost-effective and environmentally benign amide synthesis for the manufacturing of pharmaceuticals and fine chemicals”
Dr Jayasree Seayad (ICES) “Development of efficient Carbon-Carbon coupling methodology by Carbon-Hydrogen bond activation for pharmaceutical and specialty chemicals synthesis.”
A/Prof Tan Choon Hong (NUS) “Flavins as Biomimetic Organocatalysts for Green Chemistry”
A/Prof Li Zhi (NUS) “Enantioselective biotransformations for sustainable pharmaceutical production: enzyme discovery, engineering and synthetic application”
17 ‘green’ talents to be developed by initial 17 ‘green’ talents to be developed by initial projects; up to 100 over program lifetimeprojects; up to 100 over program lifetime
Next StepsNext Steps
• 2nd call for proposals
• Annual symposia
• Build strong industrial sponsorship
• Continue to grow the Green and Sustainable Manufacturing Community
Timeline Process
October 2010
Submit byDec 2010
Complete byFeb 2010
Q2 2010
RFPKick-Off
Proposal Submission
Proposal Review
AwardGrants
Do more, feel better,
live longer
Back Up Slides for MediaBack Up Slides for Media
Amide Bond Formation: The ProblemAmide Bond Formation: The Problem
N
OH
CO2H
PhNH2
N
OH
Ph
NH
O
N
OH
Ph
NH
O
Stage 2
SK&F 71130
SB 223412-A
SB 223412
SB 240108
1) EtOAc Et3N, SOCl2
2)
Stage 2 (cont.)
Slurry in TBME/Water/NaHCO3
3) conc. HCl4) HCl salt
.HCl
14 volumes
isolate
isolate
Issues: Thionyl Chloride (SOClIssues: Thionyl Chloride (SOCl22, toxic, difficult to , toxic, difficult to
use); excess base (wasted); impure product (need use); excess base (wasted); impure product (need extra purification step = wasted solvent)extra purification step = wasted solvent)
N
O
O O
NHSO2Pyr
NSO2pyr
N
OH
O
ORu
OCl
Cl
NNMes Mes
NSO2pyr
N
OH
O
O
NSO2pyr
N
OH
O
O
NSO2pyr
NH2
OH
solution
solution
N
PNN
N
toluene, 110 °C
85%
H2, Pd/C
THF, 35 oC
SB-719133MW 229.23 SB-719145
MW 441.51
SB-719138MW 413.45
SB-719147MW 414.48
SB-719150MW 285.37
stage 5stage 6
stage 7 stage 8
80%
NH2NH2-H2O
MW 212.27
isolated solidisolated solidi-PrOH, reflux
(0.005 equiv)
BTPP (5 mol%)
1.
2. acetone/IPA crystallization
ethanol, 72-75 oC
1.
2. CH2Cl2 extraction
1.
2. 80% aq. (HOCH2)4PCl,NaHCO3
3. Add H2O, cyclohexane
4. iPrOH wash
An illustrative route of synthesis
NSO2pyr
NH2
OH
NSO2pyr
NH
OH
O
NH
O
O
O
NH
O
O
OH
NSO2pyr
NH
O
O
NH
O
O
NN
NH
O
N N N
N
O
80%
SB-719150MW 285.37
SB-368560, MW 275.30
SB-576047MW 542.65
stage 9
stage 10
DMSO, Ac2O
80%
55-60 oC, 3 h
SB-462795MW 540.65
CH2Cl2,
TBME, EtOAcisolate TBME solvate
heptane
slurry, 75 oC
isolated solid
HCl.(1.0 equiv)
(1.0 equiv)
(0.05 equiv)
1.
2. toluene/TBME crystallization
crystallization
An illustrative route of synthesis (2)
