Methanol → 1-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-1h-pyrazole-4-carboxylic acid

HRID 1505287노트

반응식

HRID 1505287 반응식
C[O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:10]2[CH2:14][C:13]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)([C:15]([F:18])([F:17])[F:16])[O:12][N:11]=2)[CH:9]=1)=[O:4].[OH-].[Na+].CO>C1COCC1.O>[Cl:25][C:23]1[CH:24]=[C:19]([C:13]2([C:15]([F:18])([F:16])[F:17])[O:12][N:11]=[C:10]([N:8]3[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[N:7]3)[CH2:14]2)[CH:20]=[C:21]([Cl:26])[CH:22]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 584979541-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-1H-pyrazole-4-carboxylic acid methyl ester

생성물 1

HCID 584979271-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-1h-pyrazole-4-carboxylic acid수율 91.2%

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

실험 절차

To a solution of methyl ester of example 19.1 (513 mg) in 12.5 ml THF:water (4:1) was added sodium hydroxide (75 mg). The reaction mixture was stirred at room temperature for 3 hours before adding 2 ml of methanol. The reaction was stirred overnight before evaporation of the solvent in vacuo. The aqueous layer was extracted with ethyl acetate before being acidified. It was then extracted several times with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to afford the title acid (452 mg) as a yellow solid. 1H-NMR (CDCl3, 400 MHz): 8.55 (s, 1H), 8.05 (s, 1H), 7.50 (m, 2H), 7.45 (m, 1H), 4.35 (d, 1H), 4.00 (d, 1H).

후처리

  1. stirringThe reaction was stirred overnight before evaporation of the solvent in vacuo
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. extractionIt was then extracted several times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-67a4a8d983254ad081fcbd0c746e136c
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216973B2

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