L-Alanyl-L-proline → N-(1-carboxy-5-methylhexyl)-L-alanyl-L-proline

HRID 1758832Notes

Reaction equation

[CH3:1][CH:2]([CH3:11])[CH2:3][CH2:4][CH2:5][C:6](=O)[C:7]([OH:9])=[O:8].[NH2:12][C@H:13]([C:15]([N:17]1[CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([OH:21])=[O:20])=[O:16])[CH3:14].C([BH3-])#N.[Na+]>>[C:7]([CH:6]([NH:12][C@H:13]([C:15]([N:17]1[CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([OH:21])=[O:20])=[O:16])[CH3:14])[CH2:5][CH2:4][CH2:3][CH:2]([CH3:11])[CH3:1])([OH:9])=[O:8]

Participants

Reactant 3

HCID 83525L-Alanyl-L-proline

HCID 5003444Sodium cyanoborohydride

HCID 133897916-Methyl-2-oxoheptanoic acid

Product 1

HCID 13389793N-(1-carboxy-5-methylhexyl)-L-alanyl-L-prolineYield 64.8%

Procedure

6-Methyl-2-oxoheptanoic acid (0.90 g) and L-alanyl-L-proline (0.21 g) were treated with sodium cyanoborohydride (0.21 g) as described above. A white fluffy solid, N-(1-carboxy-5-methylhexyl)-L-alanyl-L-proline (0.24 g) was obtained. After purification by chromatography the mass spectrum showed a peak at 472 (disilyl derivative). The nmr spectrum showed absorption centered at 4.5, 3.65, 2.0, 1.6, 1.3, and 0.85 ppm.

Sources & evidence

ORD record: ord-7eee45ba4bd54a1db7a5cb328ab55293
Source dataset: uspto-grants-1983_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04374829

Reaction notes

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