1-[N-benzyloxycarbonyl-(S)-alanyl]hexhydrofuro[3,4-b]pyrrole-2(S)-carboxylic acid → 1-[(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2(S)-carboxylic acid

HRID 2226421Notes

Reaction equation

HRID 2226421 reaction equation
C(OC([NH:11][C@H:12]([C:14]([N:16]1[C@H:20]([C:21]([OH:23])=[O:22])[CH2:19][CH:18]2[CH2:24][O:25][CH2:26][CH:17]12)=[O:15])[CH3:13])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][C@H:12]([C:14]([N:16]1[C@H:20]([C:21]([OH:23])=[O:22])[CH2:19][CH:18]2[CH2:24][O:25][CH2:26][CH:17]12)=[O:15])[CH3:13]

Participants

4

Reactant 1

HCID 186548841-[N-benzyloxycarbonyl-(S)-alanyl]hexhydrofuro[3,4-b]pyrrole-2(S)-carboxylic acid

Product 1

HCID 186548901-[(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2(S)-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dissolve 1-[N-benzyloxycarbonyl-(S)-alanyl]hexhydrofuro[3,4-b]pyrrole-2(S)-carboxylic acid in methanol. Add 10% palladium-on-charcoal and hydrogenate the mixture at atmospheric pressure. Filter the mixture and concentrate in vacuo to give 1-[(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2(S)-carboxylic acid.

Workup

  1. filtrationFilter the mixture
  2. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-40d263f00cae47d9abf168bf7bf0d4ca
Source dataset
uspto-grants-1994_09
Patent number
US05348944

Reaction notes

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