Water → 1-[(4-Fluorophenyl)sulfonylamino]cyclopropanecarboxylic acid

HRID 1479854노트

반응식

HRID 1479854 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2([C:15]([O:17]C)=[O:16])[CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.O[Li].O>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2([C:15]([OH:17])=[O:16])[CH2:14][CH2:13]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 90384177Methyl 1-(4-fluorophenylsulfonamido)cyclopropanecarboxylate

생성물 1

HCID 607292541-[(4-Fluorophenyl)sulfonylamino]cyclopropanecarboxylic acid수율 98.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Compound 13A (645 mg, 2.36 mmol) dissolved in THF (10 ml) and water (5 ml) was added with LiOH.H2O (3 equiv., 297 mg) and the reaction was stirred at rt 3 hours. The reaction was concentrated under vacuum. Water was added and 10% HCl till precipitation of the acid. The acid was extracted with ethyl acetate and the organic phase was washed with Brine, dried over sodium sulfate and concentrated under vacuum to give 600 mg of 15C as a white solid. Yield=98%. 1HNMR (DMSO, 200 MHz) δ 1.38 (2H, m), 1.35 (2H, bs), 7.42 (2H, m), 7.80 (2H, m), 8.80 (1H, bs), 12.46 (1H, bs)

후처리

  1. concentrationThe reaction was concentrated under vacuum
  2. additionWater was added
  3. custom10% HCl till precipitation of the acid
  4. extractionThe acid was extracted with ethyl acetate
  5. washthe organic phase was washed with Brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-81f7e8744dd6495f81673060fef6e4e7
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409864B2

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