Sodium Hydroxide → 1-[Methyl-(4-fluorophenyl)sulfonyl-amino]cyclopropanecarboxylic acid

HRID 1479884Notes

Reaction equation

HRID 1479884 reaction equation
[CH3:1][N:2]([S:10]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[C:3]1([C:6]([O:8]C)=[O:7])[CH2:5][CH2:4]1.[OH-].[Na+]>O1CCOCC1>[CH3:1][N:2]([S:10]([C:13]1[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=1)(=[O:12])=[O:11])[C:3]1([C:6]([OH:8])=[O:7])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90390547Methyl 1-[methyl-(4-fluorophenyl)sulfonyl-amino]cyclopropanecarboxylate

Product 1

HCID 903908061-[Methyl-(4-fluorophenyl)sulfonyl-amino]cyclopropanecarboxylic acidYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 14A (1.3 g, 4.52 mmol) in dioxane (40 mL) was added with 10% NaOH aq. solution (20 mL) and the mixture was heated at 50° C. overnight. The organic solvent was removed under reduced pressure and the aqueous phase was acidified with 10% HCl. The solid formed was collected by filtration, washed with water (2×20 mL) and dried to afford 15A as white solid (1.0 g, 81% yield). 1HNMR (DMSO, 200 MHz) δ 1.40 (bs, 4H), 2.91 (s, 3H), 7.42 (m, 2H), 7.80 (m, 2H), 12.60 (bs, 1H).

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. customThe solid formed
  3. filtrationwas collected by filtration
  4. washwashed with water (2×20 mL)
  5. customdried

Sources & evidence

ORD record
ord-69c1a6bd040a471b8dd593befe29eecf
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

Loading…