Sodium Hydroxide → 2-[Ethyl-(3-fluorophenyl)sulfonyl-amino]prop-2-enoic acid

HRID 1479864Notes

Reaction equation

HRID 1479864 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]([CH2:19][CH3:20])[C@@H:12]([CH2:17]O)[C:13]([O:15]C)=[O:14])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>O1CCOCC1>[CH2:19]([N:11]([S:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)(=[O:10])=[O:9])[C:12](=[CH2:17])[C:13]([OH:15])=[O:14])[CH3:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131736600methyl (2S)-2-[(3-fluorophenyl)sulfonyl-ethyl-amino]-3-hydroxy-propanoate

Product 1

HCID 1317366012-[Ethyl-(3-fluorophenyl)sulfonyl-amino]prop-2-enoic acidYield 25%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3F (3.0 g, 9.8 mmol) in dioxane (30 mL) was added with 20% NaOH aq. solution (20 mL) and the mixture heated at 80° C. for 5 h. The organic solvent was removed under reduced pressure and the aqueous phase acidified with 10% HCl. The solid formed was filtered under vacuum, washed with cold water (1×50 mL) and dried to afford 4F as white solid (650 mg, 25% yield). 1HNMR (DMSO, 200 MHz) δ 1.11 (t, 3H, J=7.7), 3.43 (q, 2H), 5.78 (s, 1H), 6.36 (s, 1H), 7.69 (m, 2H), 7.84 (m, 2H), 12.98 (bs, 1H).

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. customThe solid formed
  3. filtrationwas filtered under vacuum
  4. washwashed with cold water (1×50 mL)
  5. customdried

Sources & evidence

ORD record
ord-9deced8009944107bc4308db842895a1
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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