Methanol → 3-Acetyl-5-((1-(4-fluorophenyl)ethyl)carbamoyl)benzoic acid

HRID 1454211노트

반응식

HRID 1454211 반응식
[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14](=[O:25])[NH:15][CH:16]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH3:17])[CH:13]=1)[C:7]([O:9]C)=[O:8])(=[O:3])[CH3:2].CO.O.[Li+].[OH-]>C1COCC1>[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14](=[O:25])[NH:15][CH:16]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH3:17])[CH:13]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 57529315Methyl 3-acetyl-5-((1-(4-fluorophenyl)ethyl)-carbamoyl)benzoate

생성물 1

HCID 575293003-Acetyl-5-((1-(4-fluorophenyl)ethyl)carbamoyl)benzoic acid수율 96%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 3-acetyl-5-((1-(4-fluorophenyl)ethyl)-carbamoyl)benzoate (302 mg, 0.88 mmol) in a mixture of THF (1.2 mL), MeOH (2.4 mL) and H2O (6.0 mL), was added LiOH (63.3 mg, 2.64 mmol) and the mixture was stirred at room temperature for 1 h. The mixture was concentrated and partitioned between ethyl acetate and H2O. The aqueous layer was washed with ethyl acetate twice and acidified with 1N HCl solution to pH around 2˜3. The aqueous layer was extracted with ethyl acetate 3 times and the combined organic layers were dried over sodium sulfate and concentrated under vacuum to give the title compound which was ready for next step without further purification (278 mg, 96% yield): HPLC retention time: 1.718 min (method A). MS (ESI) (M+H)+ 329.00.

후처리

  1. concentrationThe mixture was concentrated
  2. custompartitioned between ethyl acetate and H2O
  3. washThe aqueous layer was washed with ethyl acetate twice
  4. extractionThe aqueous layer was extracted with ethyl acetate 3 times
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-1a899f5b420e4886b1e6a53d940e5c32
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476764B2

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