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

HRID 1689826ノート

反応式

HRID 1689826 の反応式
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

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59369326HCID 59369326、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2604137ef5874f38928870656924b27c
出典データセット
uspto-grants-2012_04
特許番号
US08153624B2

反応ノート

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