2-Oxo-4-phenylbutyric acid → N-(1-carboxy-3-phenylpropyl)-L-alanyl-L-proline amide

HRID 1758855Notes

Reaction equation

HRID 1758855 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([NH2:10])=[O:9])=[O:5])[CH3:3].O=[C:15]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:16]([OH:18])=[O:17].C([BH3-])#N.[Na+]>C(O)C.O>[C:16]([CH:15]([NH:1][C@H:2]([C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([NH2:10])=[O:9])=[O:5])[CH3:3])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 697322-Oxo-4-phenylbutyric acidHCID 5003444Sodium cyanoborohydrideHCID 11902966(2S)-1-[(2S)-2-aminopropanoyl]pyrrolidine-2-carboxamide

Product 1

HCID 54134361N-(1-carboxy-3-phenylpropyl)-L-alanyl-L-proline amide

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Couple L-alanyl-L-proline amide, prepared as in Example 51, with 2-oxo-4-phenylbutyric acid employing sodium cyanoborohydride in 50% ethanol-water by the method described in example 2. After eluting from the ion-exchange resin, concentrate in vacuo to a small volume, flush with water, and freeze-dry to obtain N-(1-carboxy-3-phenylpropyl)-L-alanyl-L-proline amide as a mixture of diastereoisomers.

Workup

  1. washAfter eluting from the ion-exchange resin
  2. concentrationconcentrate in vacuo to a small volume
  3. customflush with water
  4. customfreeze-dry

Sources & evidence

ORD record
ord-084b07114f954c47ac077e5ce64d4d5b
Source dataset
uspto-grants-1983_02
Patent number
US04374829

Reaction notes

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