Triethylamine → (2S)-1-[(2S)-2-amino-3-phenylpropanoyl]pyrrolidine-2-carboxamide

HRID 1886497Notes

Reaction equation

HRID 1886497 reaction equation
Br.[NH2:2][C@H:3]([C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([NH2:17])=[O:16])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C>CN(C=O)C>[NH2:2][C@H:3]([C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([NH2:17])=[O:16])=[O:12])[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 70042899HCID 70042899, compound

Product 1

HCID 11557977(2S)-1-[(2S)-2-amino-3-phenylpropanoyl]pyrrolidine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

L-Phenylalanyl-L-prolinamide hydrobromide (480 mg) was dissolved in DMF (3 ml), to which was added triethylamine (0.29 ml) under cooling at -10° C. The mixture was stirred for 10 minutes under ice-cooling and the resultant precipitate was filtered off to give L-phenylalanyl-L-prolinamide in DMF solution, which was immediately used for the next reaction.

Workup

  1. temperaturecooling
  2. filtrationthe resultant precipitate was filtered off

Sources & evidence

ORD record
ord-e82347b47a9644c68f67226208e716bd
Source dataset
uspto-grants-1992_09
Patent number
US05151497

Reaction notes

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