HRID544042

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6228

N,N-Dimethylformamide

C3H7NO

HCID24813

Phosphoric trichloride

Cl3OP

结构：NC1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)=CCS[C@H]12

HCID12775080

未命名化合物

HCID54419337

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)CON=C(C(=O)NC1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)=CCS[C@H]12)c1csc(NC=O)n1

HCID131712477

未命名化合物

收率 90.9%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID180

Acetone

C3H6O

溶剂HCID962

Water

H2O

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

2-(2-Formamidothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetic acid (syn isomer, 1.35 g.), 4-nitrobenzyl 7-amino-3-cephem-4-carboxylate (1.54 g.), N,N-dimethylformamide (393 mg.), phosphoryl chloride (825 mg.), tetrahydrofuran (21.2 ml.), acetone (3.9 ml.) and water (3.9 ml.) were treated in a similar manner to that of Example 15-(1) to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer 2.52 g.).

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-45825716e7204304b8b8467c2abb0bc7
来源数据集: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04447430
来源说明: uspto-grants-1984_05

反应 SMILES

[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]([OH:12])=O)[N:8]=1)=[O:2].[NH2:21][CH:22]1[C:42](=[O:43])[N:24]2[C:25]([C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=3)=[O:30])=[CH:26][CH2:27][S:28][C@H:23]12.CN(C)C=O.P(Cl)(Cl)(Cl)=O>O.CC(C)=O.O1CCCC1>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]([NH:21][CH:22]2[C:42](=[O:43])[N:24]3[C:25]([C:29]([O:31][CH2:32][C:33]4[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=4)=[O:30])=[CH:26][CH2:27][S:28][C@H:23]23)=[O:12])[N:8]=1)=[O:2]