Hydrochloric Acid → 4-{4-[5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-azepan-1-yl}-benzoic acid

HRID 1689826노트

반응식

HRID 1689826 반응식
C([O:3][C:4](=[O:36])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:17][CH2:16][CH2:15][CH:14]([O:18][CH2:19][C:20]3[C:21]([C:28]4[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=4[Cl:35])=[N:22][O:23][C:24]=3[CH:25]3[CH2:27][CH2:26]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)C.[OH-].[K+].Cl>C(O)C.O1CCCC1>[CH:25]1([C:24]2[O:23][N:22]=[C:21]([C:28]3[C:29]([Cl:35])=[CH:30][CH:31]=[CH:32][C:33]=3[Cl:34])[C:20]=2[CH2:19][O:18][CH:14]2[CH2:15][CH2:16][CH2:17][N:11]([C:8]3[CH:7]=[CH:6][C:5]([C:4]([OH:36])=[O:3])=[CH:10][CH:9]=3)[CH2:12][CH2:13]2)[CH2:27][CH2:26]1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59369326HCID 59369326, 화합물

생성물 1

HCID 252047654-{4-[5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-azepan-1-yl}-benzoic acid수율 99%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

To a solution of 8.28 g (15.64 mmol) of 4-{4-[5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-azepan-1-yl}-benzoic acid ethyl ester (Isomer B) in 50 mL of Ethanol and 150 mL of tetrahydrofuran, is added potassium hydroxide (55.16 g, 78.19 mmol). The resulting mixture is stirred at 60° C. for 14 hours. The mixture is cooled to room temperature and acidified with 2N HCl to pH 5-6. The solvent is removed under vacuum, the resulting slurry is diluted with CH2Cl2 (150 mL) and washed with water (2×80 mL). The organic layer is dried (MgSO4), filtered and concentrated to afford 7.76 g of the title compound as a white solid (98%). MS (m/e): 501 (M+1).

후처리

  1. temperatureThe mixture is cooled to room temperature
  2. customThe solvent is removed under vacuum
  3. additionthe resulting slurry is diluted with CH2Cl2 (150 mL)
  4. washwashed with water (2×80 mL)
  5. dry with materialThe organic layer is dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2604137ef5874f38928870656924b27c
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153624B2

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