HRID1607711

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID176

Acetic Acid

C2H4O2

HCID516951

Monobasic potassium phosphate

H2KO4P

结构：CC(=O)OCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](NC(=S)NC(=O)OCC(Cl)(Cl)Cl)[C@H]2SC1

HCID86743374

未命名化合物

PRODUCTS

生成物

结构：CC(=O)OCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](NC(N)=S)[C@H]2SC1

HCID14349717

未命名化合物

结构：CC(=O)OCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](NC(=S)NC(=O)OCC(Cl)Cl)[C@H]2SC1

HCID86743373

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID23994

Zinc

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

A mixture of 1.16 g of (6R-trans)-3-[(acetyloxy)methyl]-8-oxo-7-[[thioxo[[(2,2,2-trichloroethoxy)carbonyl]amino]methyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester, 660 mg of zinc dust, 0.25 ml of glacial acetic acid, 2 ml of 1M aqueous potassium dihydrogen phosphate and 10 ml of tetrahydrofuran was stirred for 1 hour and then filtered. The filtrate was subjected to flash chromatography, eluting with ethyl acetate:petroleum ether in a 1:1 to 1:2 gradient, giving 340 mg of (6R-trans)-3-[(acetyloxy)methyl]-7-[(aminothioxomethyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester and 30 mg of (6R-trans)-3-[(acetyloxy)methyl]-7-[[[[(2,2-dichloroethoxy)carbonyl]amino]thioxomethyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester.

WORKUP

后处理

filtrationfiltered
washeluting with ethyl acetate

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-d4a9e43cec134390a13ad0d2283e6386
来源数据集: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04866169
来源说明: uspto-grants-1989_09

反应 SMILES

[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][C@H:11]2[N:8]([C:9](=[O:26])[C@H:10]2[NH:14][C:15](=[S:25])[NH:16][C:17]([O:19][CH2:20][C:21](Cl)([Cl:23])[Cl:22])=[O:18])[C:7]=1[C:27]([O:29][CH:30]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])(=[O:3])[CH3:2].C(O)(=O)C.P([O-])(O)(O)=O.[K+]>[Zn].O1CCCC1>[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][C@H:11]2[N:8]([C:9](=[O:26])[C@H:10]2[NH:14][C:15]([NH2:16])=[S:25])[C:7]=1[C:27]([O:29][CH:30]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:28])(=[O:3])[CH3:2].[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][C@H:11]2[N:8]([C:9](=[O:26])[C@H:10]2[NH:14][C:15]([NH:16][C:17]([O:19][CH2:20][CH:21]([Cl:22])[Cl:23])=[O:18])=[S:25])[C:7]=1[C:27]([O:29][CH:30]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:28])(=[O:3])[CH3:2]