Phenylpyruvic acid → HCID 54518889, compound

HRID 1758830Notes

Reaction equation

HRID 1758830 reaction equation
[C:1]1([CH2:7][C:8](=O)[C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][C@H:14]([C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([OH:22])=[O:21])=[O:17])[CH3:15].C([BH3-])#N.[Na+]>CO.O>[C:9]([CH:8]([NH:13][C@H:14]([C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([OH:22])=[O:21])=[O:17])[CH3:15])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 997Phenylpyruvic acidHCID 83525L-Alanyl-L-prolineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 54518889HCID 54518889, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of phenylpyruvic acid (753 mg) and L-alanyl-L-proline (171 mg) in methanol-water are adjusted to pH 6.8 and treated with sodium cyanoborohydride (173 mg) at room temperature until reaction is complete. The product is absorbed on strong cation exchange resin and eluted with 2% pyridine in water to give 294 mg of crude diastereomeric product, N-(1-carboxy-2-phenylethyl)-L-alanyl-L-proline. A portion is purified by gel filtration (LH-20) for spectrographic analysis. The nmr spectrum shows a broad singlet at 7.2, complex absorption from 3.0 to 4.6, a multiplet at 2.1 and a pair of doublets at 1.5 ppm.

Workup

  1. customThe product is absorbed on strong cation exchange resin
  2. washeluted with 2% pyridine in water

Sources & evidence

ORD record
ord-22c246ac6bb14431aafba7c2a68193be
Source dataset
uspto-grants-1983_02
Patent number
US04374829

Reaction notes

Loading…