HRID1373162

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID15413

Methyl tert-butyl ether

C5H12O

HCID24758

Sodium hydride

HNa

结构：COC(=O)c1c(C)cccc1CO[C@@H]1CCC[C@H](O)C1

HCID11492838

未命名化合物

HCID69494645

未命名化合物

PRODUCTS

生成物

结构：COC(=O)c1c(C)cccc1CO[C@@H]1CCC[C@H](OCc2nc(-c3ccc4ccccc4c3)oc2C)C1

HCID58781014

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

At room temperature, 50 mg of a 60% strength suspension of sodium hydride are added to a solution of 200 mg of methyl 2-((1R,3S)-3-hydroxycyclohexyloxy-methyl)-6-methylbenzoate in 5 ml of dimethylformamide, and 380 mg of 4-iodo-methyl-5-methyl-2-naphthalen-2-yloxazole are then added. After one hour, methyl tert-butyl ether is added and the mixture is extracted with water. The organic phase is dried over magnesium sulfate, the solvents are removed under reduced pressure and the residue is purified by RP-HPLC. This gives 94 mg of methyl 2-methyl-6-[(1R,3S)3-(5-methyl-2-naphthalen-2-yloxazol-4-ylmethoxy)cyclohexyl-oxymethyl]benzoate as a light-yellow oil.

WORKUP

后处理

additionare then added
extractionthe mixture is extracted with water
dry with materialThe organic phase is dried over magnesium sulfate
customthe solvents are removed under reduced pressure
customthe residue is purified by RP-HPLC

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-4ecf459d670d4304a72dc9ff93c37568
来源数据集: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07160911B2
来源说明: uspto-grants-2007_01

反应 SMILES

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