Hydrochloric Acid → 2-Carboxymethyl-1-(4-diethylaminophenyl)-5-(4-trifluoromethylphenoxy)indole-3-carboxylic acid

HRID 420906ノート

反応式

HRID 420906 の反応式
C([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH:13]=2)[N:8]([C:26]2[CH:31]=[CH:30][C:29]([N:32]([CH2:35][CH3:36])[CH2:33][CH3:34])=[CH:28][CH:27]=2)[C:7]=1[CH2:37][C:38]([O:40]CC)=[O:39])=[O:5])C.[OH-].[Na+].Cl>O1CCOCC1>[C:38]([CH2:37][C:7]1[N:8]([C:26]2[CH:27]=[CH:28][C:29]([N:32]([CH2:33][CH3:34])[CH2:35][CH3:36])=[CH:30][CH:31]=2)[C:9]2[C:14]([C:6]=1[C:4]([OH:5])=[O:3])=[CH:13][C:12]([O:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:20][CH:21]=1)=[CH:11][CH:10]=2)([OH:40])=[O:39]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 666576321-(4-Diethylaminophenyl)-2-ethoxycarbonylmethyl-5-(4-trifluoromethylphenoxy)indole-3-carboxylic acid ethyl ester

生成物 1

HCID 115482122-Carboxymethyl-1-(4-diethylaminophenyl)-5-(4-trifluoromethylphenoxy)indole-3-carboxylic acid

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

A mixture of 1-(4-diethylaminophenyl)-2-ethoxycarbonylmethyl-5-(4-trifluoromethylphenoxy)indole-3-carboxylic acid ethyl ester (150 mg, 0.26 mmol, see step (c) above), NaOH (aq, 2 M, 2 mL) and dioxane (2 μL) was stirred at 120° C. for 6 h, cooled and acidified with HCl (aq, 1 M) to pH 4 and extracted with EtOAc. The combined extracts were washed with water and brine, dried (Na2SO4), concentrated and purified by chromatography to give the title compound as a gray powder. Yield 90 mg (66%), mp 234-236° C.

後処理

  1. temperaturecooled
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by chromatography

出典と根拠

ORDレコード
ord-597a341369ef4ca0860a0abe90ebcd52
出典データセット
uspto-grants-2012_01
特許番号
US08097623B2

反応ノート

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