HRID2235294

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10796

Cesium carbonate

CCs2O3

HCID11745

Ethyl 2-bromoisobutyrate

C6H11BrO2

结构：O=C1C(Cc2c(Cl)cc(-c3ccc(O)cc3)cc2Cl)CCN1C1CCCCC1

HCID59299335

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)C(C)(C)Oc1ccc(-c2cc(Cl)c(CC3CCN(C4CCCCC4)C3=O)c(Cl)c2)cc1

HCID11606223

未命名化合物

收率 104.3%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

Dimethylformamide

C3H7NO

PROCEDURE

实验过程

Combine 1-Cyclohexyl-3-(3,5-dichloro-4′-hydroxy-biphenyl-4-ylmethyl)-pyrrolidin-2-one (prep 55) (0.15 g, 0.36 mmol), ethyl 2-bromoisobutyrate (0.28 g, 1.43 mmol) and Cs2CO3 (0.35 g, 1.07 mmol) in DMF (7 mL) and heat to 60° C. for 16 hours. Cool the reaction, extract with diethyl ether and water, dry (Na2SO4) and then purify by normal phase chromatography (30 to 80% gradient of ethyl acetate in hexanes) to afford 200 mg (100%) of the title compound: LC-MS (ES +) m/z=exact mass calcd for C29H35Cl2NO4 531, found 532 and 534 (M+1 and M+3, 100%).

WORKUP

后处理

temperatureCool
customthe reaction
extractionextract with diethyl ether and water
dry with materialdry (Na2SO4)
custompurify by normal phase chromatography (30 to 80% gradient of ethyl acetate in hexanes)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-8c7aa6d982004f33b64288b9ff6ab86c
来源数据集: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07713979B2
来源说明: uspto-grants-2010_05

反应 SMILES

[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][C:16]([C:20]4[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=4)=[CH:15][C:14]=3[Cl:27])[C:8]2=[O:28])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:30]([CH3:37])([CH3:36])[C:31]([O:33][CH2:34][CH3:35])=[O:32].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:34]([O:33][C:31](=[O:32])[C:30]([O:26][C:23]1[CH:24]=[CH:25][C:20]([C:16]2[CH:15]=[C:14]([Cl:27])[C:13]([CH2:12][CH:9]3[CH2:10][CH2:11][N:7]([CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)[C:8]3=[O:28])=[C:18]([Cl:19])[CH:17]=2)=[CH:21][CH:22]=1)([CH3:37])[CH3:36])[CH3:35]