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

HRID 2226420Notes

Reaction equation

HRID 2226420 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([N:16]1[C@H:20]([C:21]([O:23]CC)=[O:22])[CH2:19][CH:18]2[CH2:26][O:27][CH2:28][CH:17]12)=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([N:16]1[C@H:20]([C:21]([OH:23])=[O:22])[CH2:19][CH:18]2[CH2:26][O:27][CH2:28][CH:17]12)=[O:15])[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 867481481-[N-benzyloxycarbonyl(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2(S)-carboxylic acid, ethyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1 -[N-benzyloxycarbonyl- (S) -alanyl]hexahydrofuro[3,4 -b]pyrrole-2(S)-carboxylic acid, ethyl ester in methanol, add 2.5 N sodium hydroxide and stir the mixture at room temperature for 18 hours. Concentrate the mixture under nitrogen, dilute the residue with ice-water and then make the mixture acidic with concentrated hydrochloric acid. Extract the aqueous solution with ethyl acetate and dry the organic phase over magnesium sulfate. Concentrate the organic phase and place it on a column of silica gel. Elute with chloroform:glacial acetic acid 9:1 to give 1-[N-benzyloxycarbonyl-(S)-alanyl]hexahydrofuro[3,4-b ]pyrrole-2(S)-carboxylic acid.

Workup

  1. concentrationConcentrate the mixture under nitrogen
  2. additiondilute the residue with ice-water
  3. extractionExtract the aqueous solution with ethyl acetate
  4. dry with materialdry the organic phase over magnesium sulfate
  5. concentrationConcentrate the organic phase and place it on a column of silica gel
  6. washElute with chloroform

Sources & evidence

ORD record
ord-f3168b1de05b42f1bc4b5eb7eb2f502a
Source dataset
uspto-grants-1994_09
Patent number
US05348944

Reaction notes

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