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Purity:99%
Described is an improved and industriall...
All eight stereoisomers of saxagliptin h...
The commercial-scale synthesis of the DP...
methanesulfonic acid
[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester
(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide methane sulphonic acid
Conditions | Yield |
---|---|
In
isopropyl alcohol;
at 60 - 70 ℃;
for 5h;
|
96.7% |
In
isopropyl alcohol;
at 55 - 65 ℃;
for 3.5h;
Large scale reaction;
|
94% |
In
isopropyl alcohol;
at 60 ℃;
|
80% |
5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester
(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide methane sulphonic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps
1: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine
2: water; lithium hydroxide / ethanol
3: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
4: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
5: isopropyl alcohol / 60 °C
With
dmap; ammonia; water; diethylzinc; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; lithium hydroxide;
In
tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; isopropyl alcohol;
4: |Simmons-Smith Cyclopropanation;
|
methanesulfonic acid
[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester
5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester
(S)-ethyl N-tert-butoxycarbonylpyroglutamate
tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate
3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester
saxagliptin
(R)-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile
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