HRID1088246

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID24819

Phosphorus pentachloride

Cl5P

结构：CC(=O)CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1

HCID11781989

未命名化合物

$结构：CC(C)(C)OC(=O)CO/N=C(\C(=O)O)c1nsc(NC(=O)OC(C)(C)C)n1$

HCID13604646

未命名化合物

PRODUCTS

生成物

$结构：CC(=O)CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)/C(=N\OCC(=O)OC(C)(C)C)c3nsc(NC(=O)OC(C)(C)C)n3)[C@H]2SC1$

HCID88417246

未命名化合物

收率 103.5%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

2 次

PROCEDURE

实验过程

To a solution of 13 g of 2-(tert-butoxycarbonylamino-1,2,4-thiadiazol-3-yl)-2(Z)-(tert-butoxycarbonylmethoxyimino)acetic acid in 100 ml of dichloromethane, 7 g of phosphorus pentachloride is added and the mixture is stirred for 20 minutes under ice-cooling. The reaction mixture is evaporated to dryness and to the residue is added hexane and the solvent is evaporated off again. The residue is dissolved in 5 ml of dichloromethane and the solution is added under ice-cooling to a solution prepared by allowing 10 g of 7β-amino-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid and 16 g of N,O-bistrimethylsilylacetamide to react in 200 ml of dichloromethane at room temperature for one hour. The mixture is stirred at the same temperature for one hour and the solvent is then evaporated under reduced pressure. The residue is dissolved in 300 ml of ethyl acetate and the solution is washed with water and then dried over anhydrous magnesium sulfate. Then, the solvent is evaporated off and the residue is triturated with hexane. Insoluble substance is collected by filtration to give 23 g of 7β-[2-(5-tert-butoxycarbonylamino-1,2,4-thiadiazol-3-yl)-2(Z)-(tert-butoxycarbonylmethoxyimino)acetamido]-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid.

WORKUP

后处理

temperaturecooling
customThe reaction mixture is evaporated to dryness and to the residue
additionis added hexane
customthe solvent is evaporated off again
dissolutionThe residue is dissolved in 5 ml of dichloromethane
additionthe solution is added under ice-
temperaturecooling to a solution
customprepared
stirringThe mixture is stirred at the same temperature for one hour
customthe solvent is then evaporated under reduced pressure
dissolutionThe residue is dissolved in 300 ml of ethyl acetate
washthe solution is washed with water
dry with materialdried over anhydrous magnesium sulfate
customThen, the solvent is evaporated off
customthe residue is triturated with hexane
filtrationInsoluble substance is collected by filtration

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-8f56c653778a42f9a7df3810cbb87021
来源数据集: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04962100
来源说明: uspto-grants-1990_10

反应 SMILES

[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][N:12]=[C:11](/[C:14](=[N:18]/[O:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])/[C:15](O)=[O:16])[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:34][C@@H:35]1[C:53](=[O:54])[N:37]2[C:38]([C:50]([OH:52])=[O:51])=[C:39]([CH2:42][O:43][C:44](=[O:49])[CH2:45][C:46](=[O:48])[CH3:47])[CH2:40][S:41][C@H:36]12>ClCCl>[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][N:12]=[C:11](/[C:14](=[N:18]/[O:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])/[C:15]([NH:34][C@@H:35]2[C:53](=[O:54])[N:37]3[C:38]([C:50]([OH:52])=[O:51])=[C:39]([CH2:42][O:43][C:44](=[O:49])[CH2:45][C:46](=[O:48])[CH3:47])[CH2:40][S:41][C@H:36]23)=[O:16])[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]