HRID1866160

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

HCID22171331

未命名化合物

结构：CC(C)(C)OC(=O)N(CCc1ccc(Br)cc1)C[C@H](O)c1cccc(Cl)c1

HCID24823936

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)c1ccc(-c2ccc(CCN(C[C@H](O)c3cccc(Cl)c3)C(=O)OC(C)(C)C)cc2)c(OC)c1

HCID69056508

未命名化合物

收率 49.9%

AUXILIARIES

试剂、催化剂与溶剂

结构：c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1

催化剂HCID178418397

未命名化合物

溶剂HCID962

Water

H2O

溶剂HCID8071

未命名化合物

溶剂HCID8857

Ethyl acetate

C4H8O2

CONDITIONS

反应条件

温度: 80 °C

PROCEDURE

实验过程

To a solution of tert-butyl [2-(4-bromophenyl)ethyl]-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]carbamate (365 mg) in 1,2-dimethoxyethane (6 ml) was added [4-(ethoxycarbonyl)-2-methoxyphenyl]boronic acid (216 mg), tetrakis(triphenylphosphine)palladium (46 mg) and aqueous solution of sodium carbonate (2M, 0.85 ml), and the mixture was stirred at 80° C. for 4 hours under nitrogen. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to give ethyl 4′-[2-[(tert-butoxycarbonyl)[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]-amino]ethyl]-2-methoxy-1,1′-biphenyl-4-carboxylate (222 mg).

WORKUP

后处理

customThe organic layer was separated
washwashed with brine
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure
customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-646e77315b9d430d88459503dcb07ebb
来源数据集: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07629366B2
来源说明: uspto-grants-2009_12

反应 SMILES

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:18][C@@H:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)[OH:20])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[CH2:28]([O:30][C:31]([C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[C:35]([O:42][CH3:43])[CH:34]=1)=[O:32])[CH3:29].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:13]([O:12][C:11]([N:10]([CH2:18][C@@H:19]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1)[OH:20])[CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:36]2[CH:37]=[CH:38][C:33]([C:31]([O:30][CH2:28][CH3:29])=[O:32])=[CH:34][C:35]=2[O:42][CH3:43])=[CH:3][CH:4]=1)=[O:17])([CH3:16])([CH3:15])[CH3:14]