1-(1(S)-Benzyloxycarbonyl-3-methylbutyl)-3-azido-4-phenylazetidin-2-one → L-Phenylalanyl-L-leucine

HRID 223105

Reaction equation

HRID 223105 reaction equation
C([O:8][C:9]([C@@H:11]([N:16]1[CH:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]([N:26]=[N+]=[N-])[C:17]1=[O:29])[CH2:12][CH:13]([CH3:15])[CH3:14])=[O:10])C1C=CC=CC=1>[Pd].C(O)C>[NH2:26][C@H:18]([C:17]([NH:16][C@H:11]([C:9]([OH:10])=[O:8])[CH2:12][CH:13]([CH3:14])[CH3:15])=[O:29])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 228216711-(1(S)-Benzyloxycarbonyl-3-methylbutyl)-3-azido-4-phenylazetidin-2-one

Product 1

HCID 76808L-Phenylalanyl-L-leucine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-(1(S)-Benzyloxycarbonyl-3-methylbutyl)-3-azido-4-phenylazetidin-2-one (200 mg., 0.51 mmol) was hydrogenated in 10 ml. of ethanol at 50° C. for 19 hours under ambient pressure using a 10% Pd-C (270 mg.) as a catalyst to give D/L-phenylalanyl-L-leucine quantitatively.

Sources & evidence

ORD record
ord-420b9636b1154624a8cf612f4ce600e2
Source dataset
uspto-grants-1982_10
Patent number
US04352752

Linked notes

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