HRID1157357

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8431

1-Piperazinecarboxylic acid, ethyl ester

C7H14N2O2

HCID10868

Dicyclohexylcarbodiimide

C13H22N2

HCID75771

1-Hydroxybenzotriazole

C6H5N3O

结构：N#Cc1cccc(C[C@H](N)C(=O)O)c1.O=C1C(I)=CC(=C(c2cc(I)c([O-])c(I)c2)c2ccccc2C(=O)[O-])C=C1I.[Na+].[Na+]

HCID131727690

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)N1CCN(C(=O)[C@@H](N)Cc2cccc(C#N)c2)CC1.O=C1C(I)=CC(=C(c2cc(I)c([O-])c(I)c2)c2ccccc2C(=O)[O-])C=C1I.[Na+].[Na+]

HCID131727689

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

2 次

CONDITIONS

反应条件

温度: 10 °C

PROCEDURE

实验过程

TIPPS-3-cyano-(L)-phenylalanine (215 g; 0.435 mmol; 93% purity), ethyloxycarbonylpiperazine (68.8 g; 0.435 mmol) and 1-hydroxybenzotriazole. (13.3 g; 0.087 mol) were dissolved in 650 ml of DMF and cooled to 10° C. A solution of dicyclohexylcarbodiimide (98.7 g; 0.478 mol) in 216 ml of DMF was added dropwise over a period of 2 h and the reaction solution was stirred at RT overnight. After evaporating the solvent, the residue was dissolved in 436 ml of MTBE, the precipitate was filtered off, and the organic solution was extracted in each case 2× with 5% KHSO4, 5% NaHCO3 and distilled water. The solvent was evaporated under vacuum, toluene was added and then evaporated in a rotary evaporator and the product was dried under vacuum.

WORKUP

后处理

customAfter evaporating the solvent
dissolutionthe residue was dissolved in 436 ml of MTBE
filtrationthe precipitate was filtered off
extractionthe organic solution was extracted in each case 2× with 5% KHSO4, 5% NaHCO3
distillationdistilled water
customThe solvent was evaporated under vacuum, toluene
additionwas added
customevaporated in a rotary evaporator
customthe product was dried under vacuum

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-cc96408e3b3b4a88a325d982444d10c0
来源数据集: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07807681B2
来源说明: uspto-grants-2010_10

反应 SMILES

[CH:1]1[CH:6]=[C:5]([C:7]([C:17]2[CH:22]=[C:21]([I:23])[C:20]([O-:24])=[C:19]([I:25])[CH:18]=2)=[C:8]2[CH:14]=[C:13]([I:15])[C:11](=[O:12])[C:10]([I:16])=[CH:9]2)[C:4]([C:26]([O-:28])=[O:27])=[CH:3][CH:2]=1.[Na+:29].[Na+].[C:31]([C:33]1[CH:34]=[C:35]([CH:42]=[CH:43][CH:44]=1)[CH2:36][C@@H:37]([C:39]([OH:41])=O)[NH2:38])#[N:32].[CH2:45]([O:47][C:48]([N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1)=[O:49])[CH3:46].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[CH:1]1[CH:6]=[C:5]([C:7]([C:8]2[CH:9]=[C:10]([I:16])[C:11]([O-:12])=[C:13]([I:15])[CH:14]=2)=[C:17]2[CH:18]=[C:19]([I:25])[C:20](=[O:24])[C:21]([I:23])=[CH:22]2)[C:4]([C:26]([O-:28])=[O:27])=[CH:3][CH:2]=1.[Na+:29].[Na+:29].[CH2:45]([O:47][C:48]([N:50]1[CH2:51][CH2:52][N:53]([C:39](=[O:41])[C@H:37]([CH2:36][C:35]2[CH:42]=[CH:43][CH:44]=[C:33]([C:31]#[N:32])[CH:34]=2)[NH2:38])[CH2:54][CH2:55]1)=[O:49])[CH3:46]