HRID866869

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11593468

Ethyl hydrazinylacetate--hydrogen chloride (1/1)

C4H11ClN2O2

结构：O=CC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)C(NC(=O)Cc3cccs3)[C@H]2SC1

HCID88776158

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)CNN=CC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)C(NC(=O)Cc3cccs3)[C@H]2SC1

HCID131711156

未命名化合物

收率 69.8%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

To a solution of diphenylmethyl 3-formyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate (155 mg) in tetrahydrofuran (15 ml) is added a solution of carbethoxymethylhydrazine hydrochloride (69 mg) in water (2.5 ml), and the mixture is kept at room temperature for 2 days. The crystals obtained by concentration of the reaction mixture are collected by filtration, washed with ether and water, and dried to give diphenylmethyl 7-(2-thienylacetamido)-3-(2-carbethoxymethylhydrazono)methyl-3-cephem-4-carboxylate (129 mg). m.p. 70°-75° C. Yield: 69%. IR: νmaxNujol 3270, 1780, 1745, 1670; 1540cm-1. NMR: δd 6-DMSO (60MHz) 1.435 (6Hz) 3H, 3.52ABq (24; 17Hz) 2H, 3.48s2H, 3.60s2H, 4.17 quintet (6Hz) 2H, 4.95d(5Hz)1H, 5.70dd(8;4Hz)1H, 6.67-7.63m16H, 8.03s1H. [ α]D24.5 - 144° (c=0.340, CHCl3).

WORKUP

后处理

customThe crystals obtained by concentration of the reaction mixture
filtrationare collected by filtration
washwashed with ether and water
customdried

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-0db527d6bd5243bc981fb1107a25707d
来源数据集: uspto-grants-1978_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04101658
来源说明: uspto-grants-1978_07

反应 SMILES

[CH:1]([C:3]1[CH2:4][S:5][C@@H:6]2[CH:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C:25](=[O:36])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])=O.Cl.[C:38]([CH2:43][NH:44][NH2:45])([O:40][CH2:41][CH3:42])=[O:39]>O1CCCC1.O>[S:31]1[CH:32]=[CH:33][CH:34]=[C:30]1[CH2:29][C:28]([NH:27][CH:26]1[C:25](=[O:36])[N:7]2[C:8]([C:9]([O:11][CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:10])=[C:3]([CH:1]=[N:45][NH:44][CH2:43][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:4][S:5][C@H:6]12)=[O:35]