HRID261709

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8471

Triethylamine

C6H15N

结构：Cc1ccc(S(=O)(=O)N2C(=O)c3ccccc3C2=O)cc1

HCID214133

Phthalimide, N-(p-tolylsulfonyl)-

C15H11NO4S

结构：O=C(Cc1cccs1)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(CO)CS[C@H]12.[Na+]

HCID23695995

Desacetylcephalothin sodium

C14H13N2NaO5S2

PRODUCTS

生成物

结构：Cc1ccc(S(=O)(=O)NC(=O)c2ccccc2C(=O)OCC2=C(C(=O)[O-])N3C(=O)[C@@H](NC(=O)Cc4cccs4)[C@H]3SC2)cc1.[Na+]

HCID131711626

未命名化合物

收率 58.5%

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

In N,N-dimethylformamide (40 ml) is dissolved 7β-(2-thienylacetamido)-3-hydroxymethyl-3-cephem-4-carboxylic acid sodium salt (3.8 g), followed by the addition of N-tosylphthalimide (4.0 g) and triethylamine (2.0 ml) in that order. The mixture is stirred at room temperature for 4 hours. The reaction mixture is poured in water (100 ml) and rinsed with ethyl acetate. The aqueous layer is adjusted to pH 2.0 with dilute phosphoric acid and extracted with ethyl acetate. The extract is dried and, then, a solution of sodium 2-ethylhexanoate in isopropyl alcohol is added. By this procedure is obtained 7β-(2-thienylacetamido)-3-[2-(N-tosylcarbamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid sodium salt (4.0 g).

WORKUP

后处理

washrinsed with ethyl acetate
extractionextracted with ethyl acetate
customThe extract is dried
additiona solution of sodium 2-ethylhexanoate in isopropyl alcohol is added

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-d2f8a9e9b94c4d038ec5ea4e3f706045
来源数据集: uspto-grants-1979_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04166178
来源说明: uspto-grants-1979_08

反应 SMILES

[Na+:1].[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]([NH:10][C@@H:11]1[C:23](=[O:24])[N:13]2[C:14]([C:20]([O-:22])=[O:21])=[C:15]([CH2:18][OH:19])[CH2:16][S:17][C@H:12]12)=[O:9].[S:25]([N:35]1[C:39](=[O:40])[C:38]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:37]2[C:36]1=[O:45])([C:28]1[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=1)(=[O:27])=[O:26].C(N(CC)CC)C>CN(C)C=O.O>[Na+:1].[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]([NH:10][C@@H:11]1[C:23](=[O:24])[N:13]2[C:14]([C:20]([O-:22])=[O:21])=[C:15]([CH2:18][O:19][C:39](=[O:40])[C:38]3[CH:41]=[CH:42][CH:43]=[CH:44][C:37]=3[C:36](=[O:45])[NH:35][S:25]([C:28]3[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[CH2:16][S:17][C@H:12]12)=[O:9]