L-Proline, ethyl ester → ethyl N-[N-(p-chlorobenzoyl)-2-(2,6-dimethylanilino)acetyl]-L-prolinate

HRID 1413611Notes

Reaction equation

HRID 1413611 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]([CH2:17][C:18](O)=[O:19])[C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:16])=[O:7])=[CH:4][CH:3]=1.[NH:23]1[CH2:32][CH2:31][CH2:30][C@H:24]1[C:25]([O:27][CH2:28][CH3:29])=[O:26]>>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]([CH2:17][C:18]([N:23]2[CH2:32][CH2:31][CH2:30][C@H:24]2[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:19])[C:9]2[C:10]([CH3:16])=[CH:11][CH:12]=[CH:13][C:14]=2[CH3:15])=[O:7])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 79888L-Proline, ethyl esterHCID 20292207N-(p-chlorobenzoyl)-2-(2,6-dimethylanilino)acetic acid

Product 1

HCID 22814600ethyl N-[N-(p-chlorobenzoyl)-2-(2,6-dimethylanilino)acetyl]-L-prolinate

Procedure

Analogously to Example 1, by using equivalent quantities, reacting N-(p-chlorobenzoyl)-2-(2,6-dimethylanilino)acetic acid and ethyl L-prolinate and suitable processing produces ethyl N-[N-(p-chlorobenzoyl)-2-(2,6-dimethylanilino)acetyl]-L-prolinate (oil), saponification of which and processing of the reaction product yields N-[N-(p-chlorobenzoyl)-2-(2,6-dimethylanilino)acetyl]-L-proline (M.P. 199°).

Sources & evidence

ORD record
ord-d2801741b8154efd97664cb4afa4d623
Source dataset
uspto-grants-1981_02
Patent number
US04250183

Reaction notes

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