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

HRID 1479854Notes

Reaction equation

HRID 1479854 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-81f7e8744dd6495f81673060fef6e4e7
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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