HRID222539

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10796

Cesium carbonate

CCs2O3

结构：CCCCc1nc(Cl)c(C(=O)O)n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1

HCID46783205

2-Butyl-4-chloro-1-({2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl}methyl)-1H-imidazole-5-carboxylic acid

C41H35ClN6O2

2 次

结构：COP(=O)(OCCl)O[C@H]1CO[C@H]2[C@@H]1OC[C@H]2O[N+](=O)[O-]

HCID86652100

未命名化合物

PRODUCTS

生成物

结构：CCCCc1nc(Cl)c(C(=O)OCOP(=O)(OC)O[C@H]2CO[C@H]3[C@@H]2OC[C@H]3O[N+](=O)[O-])n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1

HCID86652101

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

Cesium carbonate (29.3 mg, 0.090 mmol) was added to a stirred, room temperature mixture of chloromethyl methyl (3S,3aS,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl phosphate (30 mg, 0.090 mmol) and 2-butyl-4-chloro-1-{[2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylic acid (Intermediate 4, 61.1 mg, 0.090 mmol) in N,N-dimethylformamide and the mixture was stirred at room temperature for overnight. The reaction was cooled, quenched with water and extracted with ethyl acetate. The organic phase was washed with saturated brine, dried (sodium sulfate), filtered and concentrated in vacuo. Chromatography over silica, eluting with 40-100% ethyl acetate/hexane afforded the separated diastereomers.

WORKUP

后处理

temperatureThe reaction was cooled
customquenched with water
extractionextracted with ethyl acetate
washThe organic phase was washed with saturated brine
dry with materialdried (sodium sulfate)
filtrationfiltered
concentrationconcentrated in vacuo
washChromatography over silica, eluting with 40-100% ethyl acetate/hexane
customafforded the separated diastereomers

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-54d471dfc6404b89ae5285a88d56b2b6
来源数据集: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08207208B2
来源说明: uspto-grants-2012_06

反应 SMILES

C(=O)([O-])[O-].[Cs+].[Cs+].[P:7]([O:14][C@H:15]1[CH2:19][O:18][C@@H:17]2[C@H:20]([O:23][N+:24]([O-:26])=[O:25])[CH2:21][O:22][C@H:16]12)([O:12][CH3:13])([O:9][CH2:10]Cl)=[O:8].[CH2:27]([C:31]1[N:32]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=3[C:53]3[N:57]([C:58]([C:71]4[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=4)([C:65]4[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=4)[C:59]4[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=4)[N:56]=[N:55][N:54]=3)=[CH:43][CH:42]=2)[C:33]([C:37]([OH:39])=[O:38])=[C:34]([Cl:36])[N:35]=1)[CH2:28][CH2:29][CH3:30]>CN(C)C=O>[CH2:27]([C:31]1[N:32]([CH2:40][C:41]2[CH:42]=[CH:43][C:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=3[C:53]3[N:57]([C:58]([C:59]4[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=4)([C:71]4[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=4)[C:65]4[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=4)[N:56]=[N:55][N:54]=3)=[CH:45][CH:46]=2)[C:33]([C:37]([O:39][CH2:10][O:9][P:7]([O:12][CH3:13])([O:14][C@H:15]2[CH2:19][O:18][C@@H:17]3[C@H:20]([O:23][N+:24]([O-:26])=[O:25])[CH2:21][O:22][C@H:16]23)=[O:8])=[O:38])=[C:34]([Cl:36])[N:35]=1)[CH2:28][CH2:29][CH3:30]