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

HRID 1479845Notes

Reaction equation

HRID 1479845 reaction equation
[CH2:1]([N:3]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C:4]1([C:7]([O:9]C)=[O:8])[CH2:6][CH2:5]1)[CH3:2].[OH-].[Na+]>O1CCOCC1>[CH2:1]([N:3]([S:11]([C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1)(=[O:12])=[O:13])[C:4]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5]1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90384146Methyl 1-[ethyl-(4-fluorophenyl)sulfonyl-amino]cyclopropanecarboxylate

Product 1

HCID 903843631-[Ethyl-(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, 4.33 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 1.10 (t, 3H, J=7.2), 1.65 (bs, 4H), 7.39 (m, 2H), 7.84 (m, 2H), 12.90 (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-8374f4f91ebc459a96aaab5cf6eb4ed4
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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