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Trifluoroacetic acid → L-Phenylalanyl-L-alanine

HRID 223103
Notes
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Reaction equation

HRID 223103 reaction equation
C([O:5][C:6]([C@@H:8]([N:10]1[C@H:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:12]([N:20]=[N+]=[N-])[C:11]1=[O:23])[CH3:9])=[O:7])(C)(C)C.[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27]>[Pd]>[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27].[NH2:20][C@H:12]([C:11]([NH:10][C@H:8]([C:6]([OH:7])=[O:5])[CH3:9])=[O:23])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 130352141-(1(S)-t-butoxycarbonylethyl)-3(S)-azido-4(R)-phenylazetidin-2-one

Product 2

HCID 6422Trifluoroacetic acidHCID 5488196L-Phenylalanyl-L-alanineYield 94%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

After 1-(1(S)-t-butoxycarbonylethyl)-3(S)-azido-4(R)-phenylazetidin-2-one (300 mg., 0.95 mmol) was stirred in trifluoroacetic acid (2 ml.) at room temperature for 15 hours, the solvent was removed by distillation under reduced pressure. The thus obtained oil (360 mg.) was hydrogenated in 25 ml. of ethanol at 50° C. for 15 hours under ambient pressure using a 10% Pd-C (300 mg.) as a catalyst to give trifluoroacetic acid salt of L-phenylalanyl-L-alanine (311 mg., yield: 94%).

Workup

  1. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-8446506b615d4f04850806817179a906
Source dataset
uspto-grants-1982_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04352752

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes