Sodium Hydroxide → 2-[Ethyl-(3,4-difluorophenyl)sulfonyl-amino]prop-2-enoic acid

HRID 1479860Notes

Reaction equation

HRID 1479860 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([CH2:20][CH3:21])[C@@H:13]([CH2:18]O)[C:14]([O:16]C)=[O:15])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].[OH-].[Na+]>O1CCOCC1>[CH2:20]([N:12]([S:9]([C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1)(=[O:10])=[O:11])[C:13](=[CH2:18])[C:14]([OH:16])=[O:15])[CH3:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131736598methyl (2S)-2-[(3,4-difluorophenyl)sulfonyl-ethyl-amino]-3-hydroxy-propanoate

Product 1

HCID 903905002-[Ethyl-(3,4-difluorophenyl)sulfonyl-amino]prop-2-enoic acidYield 44%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3G (2.8 g, 7.9 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 and extracted with CH2Cl2 (3×30 mL). The recombined organic phases were anhydrified using Na2SO4, evaporated under reduced pressure and then the resulting residue purified by flash chromatography (100% EtOAc) to obtain 4G as white solid (1 g, 44% yield). 1HNMR (DMSO, 200 MHz) δ 1.07 (t, 3H), 3.42 (q, 2H), 5.78 (s, 1H), 6.36 (s, 1H), 7.67 (m, 2H), 7.87 (m, 1H), 13.02 (bs, 1H).

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. extractionextracted with CH2Cl2 (3×30 mL)
  3. customevaporated under reduced pressure
  4. customthe resulting residue purified by flash chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-650fd35265014d50946410ba3f5d1488
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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