HRID1377200

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID311

Citric Acid

C6H8O7

HCID3939

Lithium hydroxide anhydrous

HLiO

HCID25517

未命名化合物

结构：COCCOc1ccc(C[C@H](NC(=O)OC(C)(C)C)[C@@H]2C[C@@H](Cc3ccc(OCc4ccccc4)cc3)C(=O)O2)cc1

HCID70149402

未命名化合物

PRODUCTS

生成物

结构：COCCOc1ccc(C[C@H](NC(=O)OC(C)(C)C)[C@@H](O)C[C@@H](Cc2ccc(OCc3ccccc3)cc2)C(=O)O)cc1

HCID22876399

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID887

Methanol

CH4O

溶剂HCID962

Water

H2O

溶剂HCID6344

Dichloromethane

CH2Cl2

溶剂HCID8071

未命名化合物

PROCEDURE

实验过程

3.85 g (6.68 mmol) of 5(S)-[1(S)-(Boc-amino)-2-[p-(2-methoxyethoxy)phenyl]ethyl]-3(R)-[(p-benzyloxyphenyl)methyl]dihydrofuran-2-(3H)-one in 107 ml of dimethoxyethane and 54 ml of water are hydrolysed, under a protective gas, with 26.5 ml of a 1M lithium hydroxide solution. After 17 h at RT, the reaction mixture is treated with an ice-cold mixture of 324 ml of sat. NH4Cl solution, 27 ml of 10% citric acid solution and 134 ml of methylene chloride. Methanol is added in order to dissolve the product completely. The aqueous phase is separated off and extracted 2× with methylene chloride. The organic phases are washed with saline, dried with Na2SO4 and evaporated: tRet (II)=15.8 min; FAB-MS (M+H)+ =594.

WORKUP

后处理

dissolutionto dissolve the product completely
customThe aqueous phase is separated off
extractionextracted 2× with methylene chloride
washThe organic phases are washed with saline
dry with materialdried with Na2SO4
customevaporated
customtRet (II)=15.8 min

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-3ee900bbf36f40c59f4a4fcf37a0c4dd
来源数据集: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05663200
来源说明: uspto-grants-1997_09

反应 SMILES

[C:1]([NH:8][C@H:9]([C@H:22]1[O:26][C:25](=[O:27])[C@H:24]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:31][CH:30]=2)[CH2:23]1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Li+].[NH4+].[Cl-].C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:50]>C(COC)OC.O.CO.C(Cl)Cl>[C:1]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:15][CH:16]=1)[C@@H:22]([OH:50])[CH2:23][C@@H:24]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[CH:31][CH:30]=1)[C:25]([OH:26])=[O:27])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]