HRID374314

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

HCID78457

L-Serine, O-(phenylmethyl)-

C10H13NO3

结构：CCOC(=O)[C@H](Cc1ccccc1)C[C@@H](Cc1ccccc1)C(=O)Cl

HCID14997130

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)[C@H](Cc1ccccc1)C[C@@H](Cc1ccccc1)C(=O)N[C@@H](COCc1ccccc1)C(=O)O

HCID14997131

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

PROCEDURE

实验过程

A solution of 3.3 g of O-benzyl-(S)-serine and 1.8 g of sodium carbonate in 30 ml of water at 0° is added to 2.2 g of 4-ethoxycarbonyl-(S,S)-2,4-dibenzylbutyryl chloride and the mixture is stirred at room temperature for 4 hours. The mixture is extracted with ether, and the aqueous layer is acidified with 2N hydrochloric acid. The acidic solution is extracted with ethyl acetate, washed with saturated brine, dried (magnesium sulfate), filtered and concentrated to yield N-[4-ethoxycarbonyl-(S,S)-2,4-di-benzylbutyryl]-O-benzyl-(L)-serine.

WORKUP

后处理

extractionThe mixture is extracted with ether
extractionThe acidic solution is extracted with ethyl acetate
washwashed with saturated brine
dry with materialdried (magnesium sulfate)
filtrationfiltered
concentrationconcentrated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-21cdc161b6b24cbbb65e6134b73769c9
来源数据集: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05166212
来源说明: uspto-grants-1992_11

反应 SMILES

[CH2:1]([O:8][CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:21]([O:23][C:24]([C@H:26]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:27][C@@H:28]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:29](Cl)=[O:30])=[O:25])[CH3:22]>O>[CH2:21]([O:23][C:24]([C@H:26]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:27][C@@H:28]([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:29]([NH:11][C@H:10]([C:12]([OH:14])=[O:13])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:30])=[O:25])[CH3:22]