Trifluoroacetic acid → 4-[(1S)-1-({[5-Chloro-2-(4-fluorophenoxy)pyridin-3-YL]carbonyl}amino)ethyl]benzoic acid

HRID 1293182

반응식

HRID 1293182 반응식
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([C:23]([NH:25][C@H:26]([C:28]2[CH:40]=[CH:39][C:31]([C:32]([O:34]C(C)(C)C)=[O:33])=[CH:30][CH:29]=2)[CH3:27])=[O:24])[C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:13][CH:14]=1>ClCCl>[Cl:8][C:9]1[CH:10]=[C:11]([C:23]([NH:25][C@H:26]([C:28]2[CH:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[CH:39][CH:40]=2)[CH3:27])=[O:24])[C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:13][CH:14]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 69050742tert-butyl 4-[(1S)-1-({[5-Chloro-2-(4-fluorophenoxy)pyridin-3-yl]carbonyl}amino)ethyl]benzoate

생성물 1

HCID 116830884-[(1S)-1-({[5-Chloro-2-(4-fluorophenoxy)pyridin-3-YL]carbonyl}amino)ethyl]benzoic acid수율 86%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Trifluoroacetic acid (10 mL) was added to a solution of tert-butyl 4-[(1S)-1-({[5-Chloro-2-(4-fluorophenoxy)pyridin-3-yl]carbonyl}amino)ethyl]benzoate (step 4, 2.1 g; 4.3 mmol) in dichloromethane (30 mL). The reaction mixture was stirred at room temperature until the starting material was fully consumed (4 h). The solvent and most of the trifluoroacetic acid were removed under reduced pressure. The residue was purified by flush silica gel column chromatography on silica gel (50 g) eluting with dichloromethane/methanol (20/1) and recrystallization (ethyl acetate-diisopropyl ether) to give 1.24 g, (86%) of the title compounds as white crystals: mp 198.2° C.;

후처리

  1. customwas fully consumed (4 h)
  2. customThe solvent and most of the trifluoroacetic acid were removed under reduced pressure
  3. customThe residue was purified
  4. customby flush silica gel column chromatography on silica gel (50 g)
  5. washeluting with dichloromethane/methanol (20/1) and recrystallization (ethyl acetate-diisopropyl ether)

출처 및 근거

ORD 기록
ord-3ffa0587373041ac814809117247c12c
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238714B2

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