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

HRID 1403545노트

반응식

HRID 1403545 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-776a979cc99448acbe051ad92ace86c7
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912188B2

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