L-Alanyl-L-proline → HCID 13105147, compound

HRID 2418408Notes

Reaction equation

[Na+].[CH3:2][CH:3]([CH3:9])[C:4](=O)[C:5]([O-: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])[CH:3]([CH3:9])[CH3:2])([OH:7])=[O:6]

Participants

Reactant 3

HCID 83525L-Alanyl-L-proline

HCID 27240593-Methyl-2-oxobutyric acid sodium salt

HCID 5003444Sodium cyanoborohydride

Product 1

HCID 13105147HCID 13105147, compoundYield 73.2%

Procedure

A mixture of 3-methyl-2-oxobutyric acid sodium salt (1.46 g) and L-alanyl-L-proline (0.40 g) was treated with sodium cyanoborohydride (0.41 g) as described above. Crude N-(1-carboxy-2-methylpropyl)-L-alanyl-L-proline (0.45 g) was obtained by elution from ion-exchange resin. The product melted at 131°-142°. The nmr spectrum shows complex absorption in the 4.6 to 3.3 region, a broad multiplet centered at 2.2 and doublets at 1.65 and 1.1 ppm.

Sources & evidence

ORD record: ord-81a1caea7ba8412fab9b967627a528b5
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472380

Reaction notes

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