HRID1076412

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10868

Dicyclohexylcarbodiimide

C13H22N2

HCID80170

2,5-Pyrrolidinedione, 1-hydroxy-

C4H5NO3

结构：CC(C)(C)OC[C@H](NC(=O)OCc1ccccc1)C(=O)O

HCID1715617

未命名化合物

结构：COC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CC(N)=O

HCID57097841

未命名化合物

PRODUCTS

生成物

结构：COC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](COC(C)(C)C)NC(=O)OCc1ccccc1

HCID131710201

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度: 0 °C

PROCEDURE

实验过程

8.90 g of H-Asn-Leu-OMe and 11.0 g of Z-Ser(tBu)-OH are dissolved in 100 ml of freshly distilled dimethylformamide. The solution is cooled to 0°C and 3.90 g of N-hydroxysuccinimide followed by 8.70 g of dicyclohexylcarbodiimide are added. After 30 minutes standing at 0°C and 18 hours at 25°C the precipitated dicyclohexylurea is filtered off and the filtrate is poured into 800 ml of ice water. The crystalline precipitate which hereupon separates out is dried in vacuo at 40°C and then recrystallised from methanol-water. The Z-Ser(tBu)-Asn-Leu-OMe which is hereupon obtained in an analytically pure form melts at melting point 202° - 205°C; [α]D20 =-18° (c = 1.05 in glacial acetic acid).

WORKUP

后处理

additionare added
filtrationthe precipitated dicyclohexylurea is filtered off
additionthe filtrate is poured into 800 ml of ice water
customThe crystalline precipitate which hereupon separates out is dried in vacuo at 40°C
customrecrystallised from methanol-water

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c70ae3c6a709420d9fc218f19fd2a7bc
来源数据集: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US03956260
来源说明: uspto-grants-1976_05

反应 SMILES

[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].[NH:19]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[C@H:20]([C:27](O)=[O:28])[CH2:21][O:22][C:23]([CH3:26])([CH3:25])[CH3:24].ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[NH:19]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[C@H:20]([C:27]([NH:1][C@H:2]([C:7]([NH:9][C@H:10]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5])=[O:28])[CH2:21][O:22][C:23]([CH3:24])([CH3:26])[CH3:25]