HRID1632870

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID962

Water

H2O

结构：CC(OC(=O)OCc1ccc([N+](=O)[O-])cc1)C1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)=C(S(=O)c3ncccn3)CC12

HCID20442568

未命名化合物

PRODUCTS

生成物

$结构：CC(=O)N/C=C\SC1=C(C(=O)OCc2ccc([N+](=O)[O-])cc2)N2C(=O)C(C(C)OC(=O)OCc3ccc([N+](=O)[O-])cc3)C2C1$

HCID88723757

未命名化合物

收率 52%

AUXILIARIES

试剂、催化剂与溶剂

结构：CCCCCCCCCCCCCCCC[N+](C)(C)Cc1ccccc1.[Cl-]

催化剂HCID31202

未命名化合物

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

p-Nitrobenzyl(5RS,6SR)-6-[(1RS)-1-p-nitrobenzyloxycarbonyloxyethyl]-3-(2-pyrimidylsulphinyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (230 mg) in dichloromethane (25 ml) was treated with benzyldimethyl-n-hexadecylammonium chloride (12 mg), cooled in an ice-bath, and treated with sodium Z-2-acetamidoethenylthiolate (contanimated by 1 molar equivalent NaCl) (77 mg) in water (25 ml). After stirring vigorously for 25 min. the layers were separated, and the dichloromethane layer was washed with dilute aqueous NaHCO3, followed by brine. After drying (MgSO4) the solution was evaporated in vacuo and the residue was chromatographed on silica gel (230-400 mesh ASTM), eluting with ethyl acetate to give the title compound (118 mg, 52% yield).

WORKUP

后处理

temperaturecooled in an ice-bath
customwere separated
washthe dichloromethane layer was washed with dilute aqueous NaHCO3
dry with materialAfter drying (MgSO4) the solution
customwas evaporated in vacuo
customthe residue was chromatographed on silica gel (230-400 mesh ASTM)
washeluting with ethyl acetate

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-eae508a9ffc14ede9bea75e958bd22a6
来源数据集: uspto-grants-1984_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04477662
来源说明: uspto-grants-1984_10

反应 SMILES

[N+:1]([C:4]1[CH:45]=[CH:44][C:7]([CH2:8][O:9][C:10]([O:12][CH:13]([CH:15]2[C:21](=[O:22])[N:20]3[CH:16]2[CH2:17][C:18]([S:36]([C:38]2N=CC=CN=2)=O)=[C:19]3[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[CH3:14])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH2:46]>ClCCl.[Cl-].C([N+](C)(C)CCCCCCCCCCCCCCCC)C1C=CC=CC=1>[C:19]([NH:20]/[CH:16]=[CH:38]\[S:36][C:18]1[CH2:17][CH:16]2[N:20]([C:21](=[O:22])[CH:15]2[CH:13]([O:12][C:10]([O:9][CH2:8][C:7]2[CH:44]=[CH:45][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:11])[CH3:14])[C:19]=1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24])(=[O:46])[CH3:18]