Sodium Hydroxide → (R)-2-(4-Fluorophenyl)-3-(2-(trifluoromethyl)pyrrolidin-1-yl)quinoxaline-6-carboxylic acid

HRID 1403545ノート

反応式

HRID 1403545 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[CH2:22][CH2:21][CH2:20][C@@H:19]3[C:23]([F:26])([F:25])[F:24])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:27]([O:29]C)=[O:28])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[CH2:22][CH2:21][CH2:20][C@@H:19]3[C:23]([F:26])([F:25])[F:24])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:27]([OH:29])=[O:28])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 70654237(R)-methyl 2-(4-fluorophenyl)-3-(2-(trifluoromethyl)pyrrolidin-1-yl)quinoxaline-6-carboxylate

生成物 1

HCID 70665298(R)-2-(4-Fluorophenyl)-3-(2-(trifluoromethyl)pyrrolidin-1-yl)quinoxaline-6-carboxylic acid収率 5.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a solution of (R)-methyl 2-(4-fluorophenyl)-3-(2-(trifluoromethyl)pyrrolidin-1-yl)quinoxaline-6-carboxylate (35 mg, crude) in methanol (15 mL) was added a solution of sodium hydroxide (10 mg, 0.25 mmol) in water (1 mL). The resulting solution was stirred overnight at room temperature and then concentrated in vacuo. The residue was dissolved in water (5 mL) and adjusted to pH 6 with aqueous hydrochloric acid (1N). The product was collected by filtration and purified by Prep-HPLC under the following conditions: Column, silica gel 19 mm*100 mm; mobile phase, A:B=0.05% TFA:ACN B %=35%˜100% 0˜8 mins; Detector, 5 um. 18.2 mg. (R)-2-(4-Fluorophenyl)-3-(2-(trifluoromethyl)pyrrolidin-1-yl)quinoxaline-6-carboxylic acid was obtained as a yellow solid (2 steps yield=5.3%).

後処理

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (5 mL)
  3. filtrationThe product was collected by filtration
  4. custompurified by Prep-HPLC under the following conditions
  5. custom=35%˜100% 0˜8 mins

出典と根拠

ORDレコード
ord-776a979cc99448acbe051ad92ace86c7
出典データセット
uspto-grants-2014_12
特許番号
US08912188B2

反応ノート

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