HRID615414

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8471

Triethylamine

C6H15N

HCID8857

Ethyl acetate

C4H8O2

结构：CC(C)(C)OC(=O)CON=C(C(=O)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(CCl)CS(=O)[C@H]12)c1cscn1

HCID131714108

未命名化合物

HCID178427285

未命名化合物

PRODUCTS

生成物

结构：Cc1ccc(SCC2=C(C(=O)OC(c3ccccc3)c3ccccc3)N3C(=O)C(NC(=O)C(=NOCC(=O)OC(C)(C)C)c4cscn4)[C@H]3S(=O)C2)nn1

HCID131714107

未命名化合物

收率 85.1%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

3-Mercapto-6-methylpyridazine (1 g) was added to a mixture of benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (5.0 g) in N,N-dimethylformamide (25 ml) and triethylamine (0.7 g) under ice-cooling and the mixture was stirred for 3 hours at the same temperature. The reaction mixture was added to a mixture of ethyl acetate and water. The separated organic layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to give benzhydryl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-(6-methylpyridazin-3-yl)thiomethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (4.8 g).

WORKUP

后处理

temperaturecooling
washThe separated organic layer was washed with a saturated aqueous solution of sodium chloride
dry with materialdried over magnesium sulfate
customevaporated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-5a38c86ebe254558a4def108524ed1b8
来源数据集: uspto-grants-1985_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04499088
来源说明: uspto-grants-1985_02

反应 SMILES

[SH:1][C:2]1[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[C:9]([O:13][C:14]([CH2:16][O:17][N:18]=[C:19]([C:51]1[N:52]=[CH:53][S:54][CH:55]=1)[C:20]([NH:22][CH:23]1[C:49](=[O:50])[N:25]2[C:26]([C:33]([O:35][CH:36]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:34])=[C:27]([CH2:31]Cl)[CH2:28][S:29](=[O:30])[C@H:24]12)=[O:21])=[O:15])([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C.C(OCC)(=O)C>CN(C)C=O.O>[C:9]([O:13][C:14]([CH2:16][O:17][N:18]=[C:19]([C:51]1[N:52]=[CH:53][S:54][CH:55]=1)[C:20]([NH:22][CH:23]1[C:49](=[O:50])[N:25]2[C:26]([C:33]([O:35][CH:36]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)=[O:34])=[C:27]([CH2:31][S:1][C:2]3[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=3)[CH2:28][S:29](=[O:30])[C@H:24]12)=[O:21])=[O:15])([CH3:10])([CH3:11])[CH3:12]