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

HRID 2226419Notes

Reaction equation

HRID 2226419 reaction equation
[NH:1]1[CH:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:4][CH:3]2[CH2:11][O:12][CH2:13][CH:2]12.[CH2:14]([O:21][C:22]([NH:24][C@H:25]([C:27]([OH:29])=[O:28])[CH3:26])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(OCC)(=O)C>[CH2:14]([O:21][C:22]([NH:24][C@H:25]([C:27]([N:1]1[C@@H:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:4][CH:3]2[CH2:11][O:12][CH2:13][CH:2]12)=[O:28])[CH3:26])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:14]([O:21][C:22]([NH:24][C@H:25]([C:27]([N:1]1[C@H:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:4][CH:3]2[CH2:11][O:12][CH2:13][CH:2]12)=[O:29])[CH3:26])=[O:23])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 736104N-carbobenzyloxyalanineHCID 18964789Ethyl hexahydrofuro[3,4-b]pyrrole-2-carboxylate

Product 2

HCID 867481471-[N-benzyloxycarbonyl-(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2(R)-carboxylic acid, ethyl esterHCID 867481481-[N-benzyloxycarbonyl(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2(S)-carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl hexahydrofuro[3,4-b]pyrrole-2-carboxylate in ethyl acetate add N-benzyloxycarbonyl-(S)-alanine, N-hydroxysuccinimide ester. Stir the reaction mixture at room temperature for 20 hours and concentrate it in vacuo. Place the residue on a column of silica gel (3000 g, 60-200 mesh) and elute with chloroform: ethyl acetate 10:1 to give 1-[N-benzyloxycarbonyl-(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2(R)-carboxylic acid, ethyl ester, and 1-[N-benzyloxycarbonyl(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2(S)-carboxylic acid, ethyl ester.

Workup

  1. concentrationconcentrate it in vacuo
  2. washelute with chloroform: ethyl acetate 10:1

Sources & evidence

ORD record
ord-52f7df55b32a41bbb2b76824eb69054e
Source dataset
uspto-grants-1994_09
Patent number
US05348944

Reaction notes

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