2-Oxo-4-phenylbutyric acid → HCID 13105154, compound

HRID 2418416Notes

Reaction equation

HRID 2418416 reaction equation
[C:1]1([CH2:7][CH2:8][C:9](=O)[C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:14][C@H:15]([C:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([OH:23])=[O:22])=[O:18])[CH3:16].C([BH3-])#N.[Na+]>O>[C:10]([CH:9]([NH:14][C@H:15]([C:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([OH:23])=[O:22])=[O:18])[CH3:16])[CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 697322-Oxo-4-phenylbutyric acidHCID 83525L-Alanyl-L-prolineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 13105154HCID 13105154, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-phenyl-2-oxobutyric acid (1.49 g) and L-alanyl-L-proline (0.31 g) in water are adjusted to pH 7.5 with caustic and treated with sodium cyanoborohydride (0.32 g) overnight. The product is absorbed on strong acid ion exchange resin and eluted with 2% pyridine in water to give 0.36 g of crude diastereomeric product, N-(1-carboxy-3-phenylpropyl)-L-alanyl-L-proline. A portion is purified by gel filtration (LH-20) for spectrographic analysis. The nmr spectrum in DMSO shows aromatic hydrogen at 7.20, a broad singlet at 4.30, broad multiplets at 3.0 to 3.9, 2.67 and 1.94, and a doublet at 1.23 and 1.15. The mass spectrum shows a molecular ion at 492 m/e for the ditrimethylsilylated species.

Workup

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

Sources & evidence

ORD record
ord-b9ead874aefe44b5898bb8ff98a8cbd7
Source dataset
uspto-grants-1984_09
Patent number
US04472380

Reaction notes

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