HRID2292048

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6259

2-Bromoacetophenone

C8H7BrO

HCID11430

Potassium Carbonate

CK2O3

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

PRODUCTS

生成物

结构：CC(=O)OCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](Nc3nc(-c4ccccc4)cs3)[C@H]2SC1

HCID14349724

未命名化合物

收率 101.9%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6342

Acetonitrile

C2H3N

PROCEDURE

实验过程

A mixture of 539 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, 240 mg of 2-bromo-1-phenylethanone, 85 mg of potassium carbonate and 7 ml of acetonitrile was stirred overnight, then filtered through hydrous magnesium silicate. The filtrate was evaporated, giving 660 mg of the desired compound [α]D26 =+68°±3° (c, 0.4 chloroform).

WORKUP

后处理

filtrationfiltered through hydrous magnesium silicate
customThe filtrate was evaporated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-e4c0ff49e9184048b1aa72c24feb2405
来源数据集: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04800199
来源说明: uspto-grants-1989_01

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:18])[C@H:10]2[NH:14][C:15]([NH2:17])=[S:16])[C:7]=1[C:19]([O:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])(=[O:3])[CH3:2].Br[CH2:36][C:37]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][C@H:11]2[N:8]([C:9](=[O:18])[C@H:10]2[NH:14][C:15]2[S:16][CH:36]=[C:37]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:17]=2)[C:7]=1[C:19]([O:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])(=[O:3])[CH3:2]