L-Proline 1,1-dimethylethyl ester → 1-[[(RS)-2-(ethoxycarbonyl)-3-phenylpropyl]sulphonyl]-L-proline tert-butyl ester

HRID 2294690Notes

Reaction equation

HRID 2294690 reaction equation
[CH2:1]([CH:8]([CH2:14][S:15](Cl)(=[O:17])=[O:16])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:23][C:24](=[O:30])[C@@H:25]1[CH2:29][CH2:28][CH2:27][NH:26]1)([CH3:22])([CH3:21])[CH3:20]>C(N(CC)CC)C>[C:19]([O:23][C:24](=[O:30])[C@@H:25]1[CH2:29][CH2:28][CH2:27][N:26]1[S:15]([CH2:14][CH:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:17])=[O:16])([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 6453108L-Proline 1,1-dimethylethyl esterHCID 21475177Ethyl 2-benzyl-3-chlorosulphonylpropionate

Product 1

HCID 867516351-[[(RS)-2-(ethoxycarbonyl)-3-phenylpropyl]sulphonyl]-L-proline tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In an analogous manner to that described above, by reacting ethyl 2-benzyl-3-chlorosulphonylpropionate with L-proline tert-butyl ester in the presence of triethylamine there is obtained 1-[[(RS)-2-(ethoxycarbonyl)-3-phenylpropyl]sulphonyl]-L-proline tert-butyl ester which is converted into (S)-α-[[[(S)-2-(tert-butyloxycarbonyl)-1-pyrrolidinyl]sulphonyl]methyl]hydrocinnamic acid by enzymatic hydrolysis using α-chymotrypsin.

Sources & evidence

ORD record
ord-e4b0652b12c94695aeef1e884e7e5917
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

Loading…