2-Oxo-4-phenylbutyric acid → N-(1-carboxy-3-phenylpropyl)-L-phenylalanyl-L-proline

HRID 1758847Notes

Reaction equation

O=[C:2]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([OH:5])=[O:4].[NH2:14][C@H:15]([C:23]([N:25]1[CH2:32][CH2:31][CH2:30][C@H:26]1[C:27]([OH:29])=[O:28])=[O:24])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([BH3-])#N.[Na+]>>[C:3]([CH:2]([NH:14][C@H:15]([C:23]([N:25]1[CH2:32][CH2:31][CH2:30][C@H:26]1[C:27]([OH:29])=[O:28])=[O:24])[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([OH:5])=[O:4]

Participants

Reactant 3

HCID 697322-Oxo-4-phenylbutyric acid

HCID 5003444Sodium cyanoborohydride

HCID 7020642Phe-Pro

Product 1

HCID 54222365N-(1-carboxy-3-phenylpropyl)-L-phenylalanyl-L-proline

Procedure

In the manner described in example 24, 2-oxo-4-phenylbutyric acid and L-phenylalanyl-L-proline are condensed in the presence of sodium cyanoborohydride to yield N-(1-carboxy-3-phenylpropyl)-L-phenylalanyl-L-proline.

Sources & evidence

ORD record: ord-6ef106b8cc884b4bb170c390be2c31c9
Source dataset: uspto-grants-1983_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04374829

Reaction notes

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