HRID420936

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID313

Hydrochloric Acid

ClH

HCID702

Ethanol

C2H6O

结构：CC(C)Oc1ccc(-n2c(CC(=O)O)c(C(=O)O)c3cc(Oc4ccc(C(F)(F)F)cn4)ccc32)cc1

HCID66657638

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)Cc1c(C(=O)O)c2cc(Oc3ccc(C(F)(F)F)cn3)ccc2n1-c1ccc(OC(C)C)cc1

HCID66658067

未命名化合物

PROCEDURE

实验过程

A mixture of 2-carboxymethyl-1-(4-isopropoxyphenyl)-5-(5-trifluoromethyl-2-pyridinyloxy)indole-3-carboxylic acid (85 mg, 0.16 mmol, see Example 26), EtOH (0.8 mL) and HCl (1 M in EtOH, 0.1 mL) was heated at reflux for 20 min, concentrated, diluted with water, neutralized with NaHCO3 (aq, sat) and extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), concentrated and purified by chromatography to give the title compound. Yield 45 mg (52%), mp 202° C.

WORKUP

后处理

temperaturewas heated
temperatureat reflux for 20 min
concentrationconcentrated
additiondiluted with water
extractionextracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated
custompurified by chromatography

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c6255b18a23b4f748579872f8eacd0f7
来源数据集: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08097623B2
来源说明: uspto-grants-2012_01

反应 SMILES

[C:1]([CH2:4][C:5]1[N:6]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH:35]([CH3:37])[CH3:36])=[CH:30][CH:29]=2)[C:7]2[C:12]([C:13]=1[C:14]([OH:16])=[O:15])=[CH:11][C:10]([O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=1)=[CH:9][CH:8]=2)([OH:3])=[O:2].Cl.[CH3:39][CH2:40]O>>[CH2:39]([O:2][C:1]([CH2:4][C:5]1[N:6]([C:28]2[CH:29]=[CH:30][C:31]([O:34][CH:35]([CH3:37])[CH3:36])=[CH:32][CH:33]=2)[C:7]2[C:12]([C:13]=1[C:14]([OH:16])=[O:15])=[CH:11][C:10]([O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=1)=[CH:9][CH:8]=2)=[O:3])[CH3:40]