Proline benzyl ester hydrochloride → 1-[(R)-Methoxycarbonylamino-cyclohexyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid benzyl ester

HRID 1279113Notes

Reaction equation

HRID 1279113 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[C:7]([OH:9])=O)=[O:4].Cl.[CH2:17]([O:24][C:25](=[O:31])[C@@H:26]1[CH2:30][CH2:29][CH2:28][NH:27]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([O:24][C:25]([C@@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[C:7](=[O:9])[C@H:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:31])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 2733413Proline benzyl ester hydrochlorideHCID 53880278(R)-methoxycarbonylamino-cyclohexyl-acetic acid

Product 1

HCID 538551711-[(R)-Methoxycarbonylamino-cyclohexyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid benzyl esterYield 50.5%

Procedure

Reaction of 1.24 g of (R)-methoxycarbonylamino-cyclohexyl-acetic acid and 1.40 g of (L)-proline benzyl ester hydrochloride using the procedure described for example 91b gave 1.17 g (50%) of the title compound as a colorless oil. (+)-APCI-MS: 403 (MH+).

Sources & evidence

ORD record
ord-820d20988b2d4249a5f8ecd94a10f8d7
Source dataset
uspto-grants-2002_09
Patent number
US06444672B1

Reaction notes

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