Lithium hydroxide, monohydrate → 1-(2-(2-(2-((4-(1-(tert-Butoxycarbonyl)piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxylic acid

HRID 592364노트

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HRID 592364 반응식
C[O:2][C:3]([C:5]1([C:8]2[CH:45]=[CH:44][CH:43]=[CH:42][C:9]=2[CH2:10][CH2:11][C:12]2[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][N:15]=[C:14]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([CH:29]4[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]4)=[CH:25][CH:24]=3)[N:13]=2)[CH2:7][CH2:6]1)=[O:4].O[Li].O>C1COCC1.CO.O>[C:38]([O:37][C:35]([N:32]1[CH2:33][CH2:34][CH:29]([C:26]2[CH:25]=[CH:24][C:23]([NH:22][C:14]3[N:13]=[C:12]([CH2:11][CH2:10][C:9]4[CH:42]=[CH:43][CH:44]=[CH:45][C:8]=4[C:5]4([C:3]([OH:4])=[O:2])[CH2:6][CH2:7]4)[C:17]([C:18]([F:20])([F:19])[F:21])=[CH:16][N:15]=3)=[CH:28][CH:27]=2)[CH2:30][CH2:31]1)=[O:36])([CH3:41])([CH3:39])[CH3:40]

참가 물질

6

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 86712285tert-Butyl 4-(4-((4-(2-(1-(methoxycarbonyl)cyclopropyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

생성물 1

HCID 867122861-(2-(2-(2-((4-(1-(tert-Butoxycarbonyl)piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxylic acid수율 228.7%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
40 °C

실험 절차

A solution of tert-butyl 4-(4-((4-(2-(1-(methoxycarbonyl)cyclopropyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (A4) (0.304 g, 0.487 mmol) and LiOH.H2O (204 mg, 4.87 mmol) in THF (7 mL), MeOH (7 mL) and H2O (1.5 mL) was stirred at room temperature overnight. The resulting mixture was then heated to 40° C. and stirred for 3.5 days. The volatiles were removed under reduced pressure and the residue was taken up in EtOAc (50 mL). Aqueous HCl (2 M, 50 mL) was added cautiously and the layers were separated. The aqueous phase was extracted with EtOAc (2×50 mL), and then the combined organics were washed with brine and dried over MgSO4. The solvent was removed in vacuo to give the title compound A5 as a yellow oil (680 mg, 98%); LCMS-A: rt 6.793 min; m/z 609 [M−H]−.

후처리

  1. customThe volatiles were removed under reduced pressure
  2. additionAqueous HCl (2 M, 50 mL) was added cautiously
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted with EtOAc (2×50 mL)
  5. washthe combined organics were washed with brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-ee4687652ac745f1a9f7f70314464e23
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238644B2

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