2-Oxo-4-phenylbutyric acid → HCID 178525380, compound

HRID 2418447Notes

Reaction equation

HRID 2418447 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:22]([N:24]1[CH2:31][CH2:30][CH2:29][C@H:25]1[C:26]([OH:28])=[O:27])=[O:23])[CH2:16][C:17]1[N:21]=[CH:20][NH:19][CH:18]=1.C([BH3-])#N.[Na+]>>[C:3]([CH:2]([NH:14][C@H:15]([C:22]([N:24]1[CH2:31][CH2:30][CH2:29][C@H:25]1[C:26]([OH:28])=[O:27])=[O:23])[CH2:16][C:17]1[N:21]=[CH:20][NH:19][CH:18]=1)[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([OH:5])=[O:4]

Participants

4

Reactant 3

HCID 697322-Oxo-4-phenylbutyric acidHCID 5003444Sodium cyanoborohydrideHCID 178511787HCID 178511787, compound

Product 1

HCID 178525380HCID 178525380, compound

Procedure

In the manner described in Example 54, 2-oxo-4-phenylbutyric acid and L-histidyl-L-proline are condensed in the presence of sodium cyanoborohydride to yield N-(1-carboxy-3-phenylpropyl)-L-histidyl-L-proline. The product is purified by gel filtration chromatography in methanol (LH-20). The nmr spectrum is consistent with structure. The mass spectrum shows a molecular ion at 657 for the disilylated species.

Sources & evidence

ORD record
ord-e572300ab8c44ad99c0b63fdbc2eacaf
Source dataset
uspto-grants-1984_09
Patent number
US04472380

Reaction notes

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