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

HRID 1479854ノート

反応式

HRID 1479854 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-81f7e8744dd6495f81673060fef6e4e7
出典データセット
uspto-grants-2016_08
特許番号
US09409864B2

反応ノート

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