Sodium Hydroxide → 1-[N-(1-Carboxy-3-phenylpropyl)-(S)-alanyl]hexahydrofuro-[3,4-b]pyrrole2(S)-carboxylic acid

HRID 2226423Notes

Reaction equation

HRID 2226423 reaction equation
[C:1]([CH:5]([NH:14][C@H:15]([C:17]([N:19]1[C@H:23]([C:24]([OH:26])=[O:25])[CH2:22][CH:21]2[CH2:27][O:28][CH2:29][CH:20]12)=[O:18])[CH3:16])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O:3]C)=[O:2].[OH-].[Na+]>CO>[C:1]([CH:5]([NH:14][C@H:15]([C:17]([N:19]1[C@H:23]([C:24]([OH:26])=[O:25])[CH2:22][CH:21]2[CH2:27][O:28][CH2:29][CH:20]12)=[O:18])[CH3:16])[CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 678524351-[N-(1-carbomethoxy-3-phenylpropyl)-(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2(S)-carboxylic acid

Product 1

HCID 678526021-[N-(1-Carboxy-3-phenylpropyl)-(S)-alanyl]hexahydrofuro-[3,4-b]pyrrole2(S)-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[N-(1-carbomethoxy-3-phenylpropyl)-(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2(S)-carboxylic acid (prepared as described in Example 47) in methanol, add 2.5N sodium hydroxide. After three hours, concentrate the reaction mixture and absorb it on an XAD-2 resin column and elute with water and then with methanol. Concentrate the methanol eluant to give a residue and absorb this residue on a silica gel column and elute with chloroform: methanol: 14% ammonium hydroxide 1:1:1. Concentrate the desired eluant fractions to obtain the title compound.

Workup

  1. concentrationconcentrate the reaction mixture
  2. customabsorb it on an XAD-2 resin column
  3. washelute with water
  4. concentrationConcentrate the methanol eluant
  5. customto give a residue
  6. customabsorb this residue on a silica gel column
  7. washelute with chloroform
  8. concentrationConcentrate the desired eluant fractions

Sources & evidence

ORD record
ord-c4164da9c9804790ac52e00de94740ed
Source dataset
uspto-grants-1994_09
Patent number
US05348944

Reaction notes

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