HRID2226419

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID736104

N-Benzyloxycarbonyl-L-alanine

C11H13NO4

HCID18964789

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)[C@H]1CC2COCC2N1C(=O)[C@H](C)NC(=O)OCc1ccccc1

HCID86748147

未命名化合物

HCID86748148

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

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

后处理

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

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-52f7df55b32a41bbb2b76824eb69054e
来源数据集: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05348944
来源说明: uspto-grants-1994_09

反应 SMILES

[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