76400-21-0 → HCID 18597444, compound

HRID 1981145Notes

Reaction equation

HRID 1981145 reaction equation
O=[C:2]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[C:3]([OH:5])=[O:4].[CH2:15]([O:22][C:23]([NH:25][CH2:26][CH2:27][S:28][CH2:29][CH2:30][C@@H:31]([C:33]([N:35]1[CH2:42][CH2:41][CH2:40][C@H:36]1[C:37]([OH:39])=[O:38])=[O:34])[NH2:32])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH2:15]([O:22][C:23]([NH:25][CH2:26][CH2:27][S:28][CH2:29][CH2:30][C@@H:31]([C:33]([N:35]1[CH2:42][CH2:41][CH2:40][C@H:36]1[C:37]([OH:39])=[O:38])=[O:34])[NH:32][CH:2]([C:3]([OH:5])=[O:4])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 1380210376400-21-0HCID 18597443HCID 18597443, compound

Product 1

HCID 18597444HCID 18597444, compound

Procedure

In the manner described in Examples 3, 5 and 6, 2-oxo-4-(4-chlorophenyl)butyric acid and N-[S-(2-benzyloxycarbonylaminoethyl)-L-homocysteinyl]-L-proline were condensed to afford N-[S-(2-benzyloxycarbonylaminoethyl)-N-{1-carboxy-3-(4-chlorophenyl)propyl}-L-homocysteinyl]-L-proline. This reaction was followed by the removal of the carbobenzoxy group with 30-32% HBr in glacial acetic acid to give N-[S-(2-aminoethyl)-N-{1-carboxy-3-(4-chlorophenyl)propyl}-L-homocysteinyl]-L-proline in 67% yield; a white solid on freeze drying; ms (trimethylsilyl): 672 (M+3TMS-15), 600 (M+2TMS-15), 570 (M+2TMS-CO2H), 498 (M+1TMS-CO2H).

Workup

  1. customcondensed

Sources & evidence

ORD record
ord-7d572d5ecfbc404a89a2611f4abb3a8f
Source dataset
uspto-grants-1985_04
Patent number
US04512979

Reaction notes

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