4-Methyl-2-oxovaleric acid → HCID 54525828, compound

HRID 1758833Notes

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

Participants

Reactant 3

HCID 704-Methyl-2-oxovaleric acid

HCID 83525L-Alanyl-L-proline

HCID 5003444Sodium cyanoborohydride

Product 1

HCID 54525828HCID 54525828, compound

Procedure

4-Methyl-2-oxopentanoic acid (1.29 g) and L-alanyl-L-proline (0.32 g) were treated with sodium cyanoborohydride (0.32 g) as described above. A fluffy white solid, N-(1-carboxy-3-methylbutyl)-L-alanyl-L-proline, was obtained (0.40 g). A portion was purified by chromatography. The mass spectrum showed a peak at 429 (molecular ion of disilyl derivative minus methyl, 444-15). The nmr spectrum showed resonances centered at 4.4, 3.6, 2.1, 1.6, and 0.95 ppm.

Sources & evidence

ORD record: ord-6b7cbdd0a9424a6398ab63b604cce3df
Source dataset: uspto-grants-1983_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04374829

Reaction notes

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