Sodium cyanoborohydride → HCID 178500038, compound

HRID 1758859Notes

Reaction equation

HRID 1758859 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C@H:4]([CH2:6][C:7]1[N:11]=[CH:10][NH:9][CH:8]=1)[NH2:5].[C:13]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([OH:22])=[O:21])(=[O:17])[C:14]([CH3:16])=O.C([BH3-])#N.[Na+]>>[CH3:1][O:2][C:3]([CH:4]([NH:5][CH:14]([C:13]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([OH:22])=[O:21])=[O:17])[CH3:16])[CH2:6][C:7]1[N:11]=[CH:10][NH:9][CH:8]=1)=[O:12]

Participants

4

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 10130260(S)-1-(2-Oxopropanoyl)pyrrolidine-2-carboxylic acidHCID 178501495HCID 178501495, compound

Product 1

HCID 178500038HCID 178500038, compound

Procedure

In a manner similar to Example 16, L-histidine methyl ester is condensed with pyruvoyl-L-proline in the presence of sodium cyano borohydride to yield N-[1-methoxycarbonyl-2-(1H-imidazol-4-yl)ethyl]-DL-alanyl-L-proline. The nmr spectrum in D2O shows the imidazole protons at 8.6 and 7.3; the protons adjacent to the imidazole and the methyl ester protons at 3.7 and the alanyl methyl at 1.1 to 1.38.

Sources & evidence

ORD record
ord-943a3d903cd5424aa388ef05fdc210ca
Source dataset
uspto-grants-1983_02
Patent number
US04374829

Reaction notes

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