4-Methyl-2-oxovaleric acid → HCID 178446425, compound

HRID 1758858Notes

Reaction equation

[CH3:1][CH:2]([CH3:9])[CH2:3][C:4](=O)[C:5]([OH:7])=[O:6].[NH2:10][C@H:11]([C:19]([NH:21][C@H:22]([C:30]([OH:32])=[O:31])[CH2:23][CH2:24][CH2:25][NH:26][C:27](=[NH:29])[NH2:28])=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([BH3-])#N.[Na+]>>[C:5]([CH:4]([NH:10][C@H:11]([C:19]([NH:21][C@H:22]([C:30]([OH:32])=[O:31])[CH2:23][CH2:24][CH2:25][NH:26][C:27](=[NH:28])[NH2:29])=[O:20])[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:3][CH:2]([CH3:9])[CH3:1])([OH:7])=[O:6]

Participants

Reactant 3

HCID 704-Methyl-2-oxovaleric acid

HCID 5003444Sodium cyanoborohydride

HCID 178512889HCID 178512889, compound

Product 1

HCID 178446425HCID 178446425, compound

Procedure

In the manner described in Example 54, 4-methyl-2-oxopentanoic acid and L-phenylalanyl-L-arginine are condensed in the presence of sodium cyanoborohydride to yield N-(1-carboxy-3-methylbutyl)-L-phenylalanyl-L-arginine. The product is eluted from the ion exchange resin with 10% ammonia. The nmr spectrum in D2O gave a singlet at 7.2 (5H), a broad triplet centered at 3.0 (6H), a broad multiplet at 1.3 (6H), and a broad doublet at 0.9 (6H).

Sources & evidence

ORD record: ord-3c0673bc4c8b4373a44b41bf1606dfc3
Source dataset: uspto-grants-1983_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04374829

Reaction notes

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