HRID270154

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11776

Triphenylphosphine

C18H15P

HCID5363146

Diisopropyl azodicarboxylate

C8H14N2O4

HCID12042519

3-(5-methyl-1,2,4-oxadiazol-3-yl)phenol

C9H8N2O2

结构：CCOC(=O)COc1ccc(SCc2sc(-c3ccc(C(F)(F)F)cc3)nc2CO)cc1C

HCID86591789

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)COc1ccc(SCc2sc(-c3ccc(C(F)(F)F)cc3)nc2COc2cccc(-c3noc(C)n3)c2)cc1C

HCID86591788

未命名化合物

收率 76.3%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID1140

Toluene

C7H8

PROCEDURE

实验过程

To a stirred solution of ethyl [4-({[4-(hydroxymethyl)-2-(4-{trifluoromethyl}phenyl)-1,3-thiazol-5-yl]methyl}sulfanyl)-2-methylphenoxy]acetate (40mg, 0.08mmoles, 1eq) in dry toluene (2ml) was added 3-(5-methyl-1,2,4-oxadiazol-3-yl)phenol (15mg, 0.088mmoles, 1.1eq) followed by triphenylphosphine (25mg, 0.096mmoles, 1.2eq) as a solid. Diisopropylazodicarboxylate (0.017ml, 0.088mmoles, 1.1eq) was then added dropwise and the reaction was stirred for 2hours at room temperature. The reaction was then partitioned between EtOAc and H2O. After the separation of the phases the organic phase washed with 0.1N NaOH, brine, dried over Na2SO4, filtered, concentrated in vacuo and purified via flash chromatography (10% EtOAc/Hexanes to 35% EtOAc/Hexanes) to yield 40mg (76%) of product.

WORKUP

后处理

customThe reaction was then partitioned between EtOAc and H2O
customAfter the separation of the phases the organic phase
washwashed with 0.1N NaOH, brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
custompurified via flash chromatography (10% EtOAc/Hexanes to 35% EtOAc/Hexanes)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-3a08f893d6314f1dba3850155675d862
来源数据集: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07449468B2
来源说明: uspto-grants-2008_11

反应 SMILES

[OH:1][CH2:2][C:3]1[N:4]=[C:5]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[S:6][C:7]=1[CH2:8][S:9][C:10]1[CH:22]=[CH:21][C:13]([O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:12]([CH3:23])[CH:11]=1.[CH3:34][C:35]1[O:39][N:38]=[C:37]([C:40]2[CH:41]=[C:42](O)[CH:43]=[CH:44][CH:45]=2)[N:36]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[CH3:23][C:12]1[CH:11]=[C:10]([S:9][CH2:8][C:7]2[S:6][C:5]([C:24]3[CH:25]=[CH:26][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:28][CH:29]=3)=[N:4][C:3]=2[CH2:2][O:1][C:42]2[CH:43]=[CH:44][CH:45]=[C:40]([C:37]3[N:36]=[C:35]([CH3:34])[O:39][N:38]=3)[CH:41]=2)[CH:22]=[CH:21][C:13]=1[O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]