HRID1528988

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：Cc1noc(-c2ccc(Br)cc2)c1C(O)COCc1ccccc1

HCID66577358

未命名化合物

结构：CCOC(=O)[C@@H]1C[C@@H]1c1ccc(B2OC(C)(C)C(C)(C)O2)cc1

HCID66578588

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)[C@@H]1C[C@@H]1c1ccc(-c2ccc(-c3onc(C)c3[C@@H](O)COCc3ccccc3)cc2)cc1

HCID66578269

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID702

Ethanol

C2H6O

PROCEDURE

实验过程

Prepared according to the procedure described in Example 110, Step 3, using 2-benzyloxy-1-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]ethanol and (cis)-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester. After the reaction the crude material was dissolved in EtOH (3 mL) and purified via preparatory chiral HPLC (Chiralcel-AD column, 8% EtOH in hexanes, 70 minutes) to afford three separate compounds. The first compound off of the column, containing a mixture of cis-cyclopropyl diastereomers, was the title compound.

WORKUP

后处理

customPrepared
custompurified via preparatory chiral HPLC (Chiralcel-AD column, 8% EtOH in hexanes, 70 minutes)
customto afford three
customseparate compounds
additionThe first compound off of the column, containing
additiona mixture of cis-cyclopropyl diastereomers

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-7834b590238647ecb7c51c7cad7189fa
来源数据集: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09090573B2
来源说明: uspto-grants-2015_07

反应 SMILES

[CH2:1]([O:8][CH2:9][CH:10]([C:12]1[C:13]([CH3:24])=[N:14][O:15][C:16]=1[C:17]1[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([O:27][C:28]([C@@H:30]1[CH2:32][C@@H:31]1[C:33]1[CH:38]=[CH:37][C:36](B2OC(C)(C)C(C)(C)O2)=[CH:35][CH:34]=1)=[O:29])[CH3:26]>CCO>[CH2:25]([O:27][C:28]([C@@H:30]1[CH2:32][C@@H:31]1[C:33]1[CH:38]=[CH:37][C:36]([C:20]2[CH:21]=[CH:22][C:17]([C:16]3[O:15][N:14]=[C:13]([CH3:24])[C:12]=3[C@@H:10]([OH:11])[CH2:9][O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:18][CH:19]=2)=[CH:35][CH:34]=1)=[O:29])[CH3:26]