Lithium Hydroxide → HCID 67983850, 화합물

HRID 1748221노트

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HRID 1748221 반응식
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][C:16]([F:19])([F:18])[F:17])[C:5]=2[CH2:20][O:21][CH:22]2[CH2:28][CH:27]3[N:29]([C:30]4[CH:42]=[CH:41][C:33]5[C:34]([C:37]([O:39]C)=[O:38])=[N:35][S:36][C:32]=5[CH:31]=4)[CH:24]([CH2:25][CH2:26]3)[CH2:23]2)[CH2:3][CH2:2]1.[Li+].[OH-]>C1COCC1.CO.O>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][C:16]([F:17])([F:19])[F:18])[C:5]=2[CH2:20][O:21][CH:22]2[CH2:28][CH:27]3[N:29]([C:30]4[CH:42]=[CH:41][C:33]5[C:34]([C:37]([OH:39])=[O:38])=[N:35][S:36][C:32]=5[CH:31]=4)[CH:24]([CH2:25][CH2:26]3)[CH2:23]2)[CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 67983726HCID 67983726, 화합물

생성물 1

HCID 67983850HCID 67983850, 화합물

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

실험 절차

Methyl 6-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]isothiazole-3-carboxylate (37 mg, 0.062 mg) in a 3:2:1 THF-MeOH—H2O solution (1 mL) was treated with a 6N LiOH solution (85 μL, 0.49 mmol) at rt for 12 hours. After this time the organic was removed in vacuo and the residue was diluted with water (1 mL.) and cooled in ice. 3N NaOH was added dropwise until pH 7. The solid that separated was collected by filtration, washed with additional water and dried in vacuo to afford the 6-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]isothiazole-3-carboxylic acid as off white solid. 1H NMR (400 MHz, DMSO) δ 8.31 (d, J=8.0 Hz, 1H), 7.68-7.62 (m, 2H), 7.57-7.52 (m, 2H), 7.18 (bs, 1H), 6.90 (d, J=9.2 Hz, 1H), 4.31 (s, 2H), 4.18 (bs, 2H), 3.42 (m, 1H), 1.88-1.84 (m, 2H), 1.80 (1.78 (m, 4H), 1.53-1.49 (m, 2H), 1.15-1.03 (m, 5H). MS m/z 586.2 (M+1).

후처리

  1. customAfter this time the organic was removed in vacuo
  2. additionthe residue was diluted with water (1 mL.)
  3. temperaturecooled in ice
  4. addition3N NaOH was added dropwise until pH 7
  5. customThe solid that separated
  6. filtrationwas collected by filtration
  7. washwashed with additional water
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-bc2b47419b6642e6a62b233b6164f2c0
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150568B2

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