HRID235745

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CC(C)(OC(=O)OCc1ccc([N+](=O)[O-])cc1)[C@H]1C(=O)N[C@@H]1CC(=O)C(=[N+]=[N-])C(=O)OCc1ccc([N+](=O)[O-])cc1

HCID86738874

未命名化合物

PRODUCTS

生成物

结构：CC(C)(OC(=O)OCc1ccc([N+](=O)[O-])cc1)[C@H]1C(=O)N2[C@@H](C(=O)OCc3ccc([N+](=O)[O-])cc3)C(=O)C[C@H]12

HCID22823193

未命名化合物

收率 86.7%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID21674

Acetic acid, rhodium(2+) salt

C4H6O4Rh

溶剂HCID241

Benzene

C6H6

PROCEDURE

实验过程

A mixture of 4-nitrobenzyl 2-diazo-4-[(2R,3S)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate (58.0 mg) and rhodium (II) acetate (0.1 mg) in benzene (3.4 ml) was refluxed for 30 minutes. After cooling to ambient temperature, the mixture was filtered with a diatomaceous earth and evaporated to give 4-nitrobenzyl (2R,5R,6S)-3,7-dioxo-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-1-azabicyclo[3.2.0]-heptane-2-carboxylate (47.8 mg) as an amorphous solid.

WORKUP

后处理

temperaturewas refluxed for 30 minutes
filtrationthe mixture was filtered with a diatomaceous earth
customevaporated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c302a43fedc04fc1856c1bed8824d33b
来源数据集: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04640915
来源说明: uspto-grants-1987_02

反应 SMILES

[N+](=[C:3]([C:17](=[O:41])[CH2:18][C@@H:19]1[C@@H:22]([C:23]([CH3:39])([O:25][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=2)=[O:27])[CH3:24])[C:21](=[O:40])[NH:20]1)[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[O:5])=[N-]>C1C=CC=CC=1.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[O:41]=[C:17]1[CH2:18][C@H:19]2[N:20]([C:21](=[O:40])[C@@H:22]2[C:23]([CH3:39])([O:25][C:26]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=2)=[O:27])[CH3:24])[C@H:3]1[C:4]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=1)=[O:5]