HRID1755891

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CC(C)(ON)C(=O)NNC(=O)c1ccc(O)c(O)c1.Cl

HCID19917907

未命名化合物

结构：Nc1nc(C(=O)C(=O)N[C@@H]2C(=O)N3C(C(=O)O)=C(CS(=O)(=O)c4ccc(O)c(O)c4)CS[C@H]23)cs1

HCID86748861

未命名化合物

PRODUCTS

生成物

$结构：CC(C)(O/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(CS(=O)(=O)c3ccc(O)c(O)c3)CS[C@H]12)c1csc(N)n1)C(=O)NNC(=O)c1ccc(O)c(O)c1$

HCID88420275

未命名化合物

收率 84.2%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID31374

Dimethylacetamide

C4H9NO

PROCEDURE

实验过程

(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[(3,4-dihydroxyphenyl)sulphonyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (160 mg) (0.30 mmol) are dissolved in 2.0 ml of dimethylacetamide, treated with 130 mg (0.39 mmol) of 1-[2-(aminooxy)-2-methylpropionyl]-2-(3,4-dihydroxybenzoyl)hydrazine hydrochloride and stirred at room temperature for 20 hours. The dimethylacetamide is evaporated under a high vacuum and the product is precipitated by the addition of water. The purification is effected by chromatography on silica gel with water/acetonitrile as the eluent. After lyophilization there are obtained 200 mg of (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]acetamido]-3-[[(3,4-dihydroxyphenyl)sulphonyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a white solid.

WORKUP

后处理

customThe dimethylacetamide is evaporated under a high vacuum
customthe product is precipitated by the addition of water
customThe purification

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-e4e8ce362a004fb9b81f172a65b60813
来源数据集: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05438052
来源说明: uspto-grants-1995_08

反应 SMILES

[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=O)[C:8]([NH:10][C@@H:11]2[C:18](=[O:19])[N:17]3[C@@H:12]2[S:13][CH2:14][C:15]([CH2:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([OH:34])[CH:28]=2)(=[O:26])=[O:25])=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1.Cl.[NH2:37][O:38][C:39]([CH3:55])([CH3:54])[C:40]([NH:42][NH:43][C:44](=[O:53])[C:45]1[CH:50]=[CH:49][C:48]([OH:51])=[C:47]([OH:52])[CH:46]=1)=[O:41]>CC(N(C)C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:37]/[O:38][C:39]([C:40](=[O:41])[NH:42][NH:43][C:44](=[O:53])[C:45]2[CH:50]=[CH:49][C:48]([OH:51])=[C:47]([OH:52])[CH:46]=2)([CH3:54])[CH3:55])/[C:8]([NH:10][C@@H:11]2[C:18](=[O:19])[N:17]3[C@@H:12]2[S:13][CH2:14][C:15]([CH2:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([OH:34])[CH:28]=2)(=[O:26])=[O:25])=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1