HRID615413

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID70297

Benzenecarboperoxoic acid, 3-chloro-

C7H5ClO3

反应SMILES：CC(C)(C)OC(=O)CON=C(C(=O)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(CSc3ccc4nncn4n3)CS[C@H]12)c1cscn1

HCID131714105

未命名化合物

HCID131714106

未命名化合物

PRODUCTS

产物

反应SMILES：CC(C)(C)OC(=O)CON=C(C(=O)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(CSc3ccc4nncn4n3)CS(=O)[C@H]12)c1cscn1

HCID131714104

未命名化合物

收率 91%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8857

Ethyl acetate

C4H8O2

2 次

PROCEDURE

实验过程

A solution of m-chloroperbenzoic acid (0.4 g) (purity: 80%) in ethyl acetate (5 ml) was added to a solution of a mixture (1.4 g) of benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylate (syn isomer) and benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)thiomethyl-2-cephem-4-carboxylate (syn isomer) in ethyl acetate (10 ml) under ice-cooling and the resultant mixture was stirred for 1 hour at the same temperature. The resulting solution was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, successively. The organic layer was dried over magnesium sulfate and evaporated to give benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (1.3 g).

WORKUP

后处理

temperaturecooling
washThe resulting solution was washed with a saturated aqueous solution of sodium bicarbonate
dry with materialThe organic layer was dried over magnesium sulfate
customevaporated

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-cf62f555e50f44d9948a7609d206261c
来源数据集: uspto-grants-1985_02
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US04499088
来源说明: uspto-grants-1985_02

反应SMILES

ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([O:16][C:17]([CH2:19][O:20][N:21]=[C:22]([C:62]1[N:63]=[CH:64][S:65][CH:66]=1)[C:23]([NH:25][CH:26]1[C:60](=[O:61])[N:28]2[C:29]([C:44]([O:46][CH:47]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[O:45])=[C:30]([CH2:33][S:34][C:35]3[CH:36]=[CH:37][C:38]4[N:39]([CH:41]=[N:42][N:43]=4)[N:40]=3)[CH2:31][S:32][C@H:27]12)=[O:24])=[O:18])([CH3:15])([CH3:14])[CH3:13].C(OC(CON=C(C1N=CSC=1)C(NC1C(=O)N2C(C(OC(C3C=CC=CC=3)C3C=CC=CC=3)=O)C(CSC3C=CC4N(C=NN=4)N=3)=CS[C@H]12)=O)=O)(C)(C)C>C(OCC)(=O)C>[C:12]([O:16][C:17]([CH2:19][O:20][N:21]=[C:22]([C:62]1[N:63]=[CH:64][S:65][CH:66]=1)[C:23]([NH:25][CH:26]1[C:60](=[O:61])[N:28]2[C:29]([C:44]([O:46][CH:47]([C:54]3[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=3)[C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)=[O:45])=[C:30]([CH2:33][S:34][C:35]3[CH:36]=[CH:37][C:38]4[N:39]([CH:41]=[N:42][N:43]=4)[N:40]=3)[CH2:31][S:32](=[O:9])[C@H:27]12)=[O:24])=[O:18])([CH3:15])([CH3:13])[CH3:14]