Sodium Hydroxide → 2-[(4-Fluorophenyl)sulfonyl-methyl-amino]prop-2-enoic acid

HRID 1479805Notes

Reaction equation

HRID 1479805 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:19])[C@@H:12]([CH2:17]O)[C:13]([O:15]C)=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH3:19])[C:12](=[CH2:17])[C:13]([OH:15])=[O:14])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131736580methyl (2S)-2-[(4-fluorophenyl)sulfonyl-methyl-amino]-3-hydroxy-propanoate

Product 1

HCID 1317365812-[(4-Fluorophenyl)sulfonyl-methyl-amino]prop-2-enoic acidYield 56.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 3A (2.3 g, 7.2 mmol) in dioxane (35 mL) was added with 20% NaOH aq. solution (20 mL) and the mixture was heated at 50° C. for 2 h. The organic solvent was removed under reduced pressure and the aqueous phase acidified with 10% HCl. The solid formed was collected by filtration, washed with water (2×20 mL) and dried to obtain 4A as white solid (1.05 g, 51% yield). 1HNMR (DMSO, 200 MHz) δ 2.92 (s, 3H), 5.57 (s, 1H), 6.09 (s, 1H), 7.50 (m, 2H), 7.85 (m, 2H), 13.01 (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-968b33742966495c8bf5a49a9ef65b22
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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