HRID2082612

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8471

Triethylamine

C6H15N

HCID75771

1-Hydroxybenzotriazole

C6H5N3O

反应SMILES：CON=C(C(=O)O)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1

HCID2724510

(Methoxyimino){2-[(triphenylmethyl)amino]-1,3-thiazol-4-yl}acetic acid

C25H21N3O3S

反应SMILES：CC(=O)OCC1=C(C(=O)OC(C)(C)C)N2C(=O)C(N)C2SC1

HCID11771800

未命名化合物

PRODUCTS

产物

反应SMILES：CON=C(C(=O)NC1C(=O)N2C(C(=O)OC(C)(C)C)=C(COC(C)=O)CSC12)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1

HCID76083774

未命名化合物

收率 76%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

2 次

PROCEDURE

实验过程

To a stirred suspension of 48 g (0.1 mole) of 2-[2-(tritylamino)thiazole-4-yl]-2-methoxyiminoacetic acid in 750 mL of anhydrous dichloromethane was added 13.94 mL (0.1 mole) of triethylamine and the mixture was mechanically stirred until a clear solution formed (approx. 45 min). After complete dissolution 20.6 g (0.1 mole) of N,N-dicyclohexylcarbodiimide and 13.5 g (0.1 mole) of 1-hydroxybenzotriazole were added and the mixture stirred at ambient temperature for 2 hours. A solution of 32.8 g (0.1 mole) of [6R-[6 alpha,7 beta(z)]]-3-(acetoxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2 carboxylic acid 1,1-dimethylethyl ester (from Example 1) in 250 mL of anhydrous dichloromethane was added and the resulting solution was stirred overnigh (16 hours) at ambient temperature. The precipitate was removed by filtration and the filtrate was washed successively with 2×250 mL=500 mL of saturated aqueous sodium bicarbonate and 2×250 mL=500 mL of saturated aqueous sodium chloride and dried over sodium sulphate. Removal of the dichloromethane afforded the crude product as a gummy-oil which was purified by preparative liquid chromatography (0-10% EtoAc in CH2Cl2), to give 57.2 g (76%) of pale yellow solid. NMR (CDCl3): 1.54 (s) 9H (t-bu) 2.09 (s) 3H (OAc); 3.35, 3.56 (d of d, J=18 Hz) 2H (CH2S); 4.08 (s) 3H (OCH3); 4.86 5.04 (d of d, J=14 Hz) 2H (CH2O); 5.04 (d, J=6 Hz) 1H (C6); 5.93 (d of d, J=6 Hz J=10 Hz), 1H (C7); 6.71 (s) 1H (thiazole); 6.91 (d, J=10 Hz) 1H (NH); 7.08 (s) 1H (NH); 7.30 (s) 15H (CPh3).

WORKUP

后处理

customformed (approx. 45 min)
additionwere added
stirringthe mixture stirred at ambient temperature for 2 hours
stirringthe resulting solution was stirred overnigh (16 hours) at ambient temperature
customThe precipitate was removed by filtration
washthe filtrate was washed successively with 2×250 mL=500 mL of saturated aqueous sodium bicarbonate and 2×250 mL=500 mL of saturated aqueous sodium chloride
dry with materialdried over sodium sulphate
customRemoval of the dichloromethane
customafforded the crude product as a gummy-oil which
customwas purified by preparative liquid chromatography (0-10% EtoAc in CH2Cl2)

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-8e9f44a614bb4d3892ca21f9b168d046
来源数据集: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US05189157
来源说明: uspto-grants-1993_02

反应SMILES

[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH3:32])[C:27](O)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.[CH3:50][C:51]([O:54][C:55]([C:57]1[N:58]2[CH:61]([S:62][CH2:63][C:64]=1[CH2:65][O:66][C:67](=[O:69])[CH3:68])[CH:60]([NH2:70])[C:59]2=[O:71])=[O:56])([CH3:53])[CH3:52]>ClCCl>[CH3:53][C:51]([O:54][C:55]([C:57]1[N:58]2[CH:61]([S:62][CH2:63][C:64]=1[CH2:65][O:66][C:67](=[O:69])[CH3:68])[CH:60]([NH:70][C:27](=[O:28])[C:26](=[N:30][O:31][CH3:32])[C:24]1[N:25]=[C:21]([NH:20][C:1]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:22][CH:23]=1)[C:59]2=[O:71])=[O:56])([CH3:50])[CH3:52]