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

HRID 1479800

Reaktionsgleichung

Reaktionsgleichung von HRID 1479800
[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@@H:4]([CH2:9]O)[C:5]([O:7]C)=[O:6])[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:13])=[O:12])[C:4](=[CH2:9])[C:5]([OH:7])=[O:6])[CH3:2]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 131736579methyl (2S)-2-[ethyl-(4-fluorophenyl)sulfonyl-amino]-3-hydroxy-propanoate

Produkt 1

HCID 903842012-[Ethyl-(4-fluorophenyl)sulfonyl-amino]prop-2-enoic acidAusbeute 71,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 3B (1.1 g, 3.6 mmol) in dioxane (25 mL) was added with 20% NaOH aq. solution (20 mL) and the mixture heated at 80° C. for 4 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 combined organic phases were dried using Na2SO4, evaporated under reduced pressure and then the resulting residue purified by flash chromatography (100% EtOAc) to obtain 4B as white solid (0.7 g, 66% yield). 1HNMR (DMSO, 200 MHz) δ 1.12 (t, 3H), 3.29 (q, 2H), 5.69 (s, 1H), 6.32 (s, 1H), 7.39 (m, 2H), 7.89 (m, 2H), 12.9 (bs, 1H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-292ee0f14b2147f98b8b4574d6453987
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409864B2

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