Hydrochloric Acid → 3-Acetyl-2-{2-[(tert-butoxycarbonyl)amino]ethoxy}-5-chloro-6-methylbenzoic acid

HRID 626822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626822
[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[C:8]([CH:21]=[O:22])[C:7]([CH3:23])=[C:6]([Cl:24])[CH:5]=1)(=[O:3])[CH3:2].[OH-:25].[Na+].Cl>CO.O.OO.NC(N)=O>[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][NH:13][C:14]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:20])=[C:8]([C:7]([CH3:23])=[C:6]([Cl:24])[CH:5]=1)[C:21]([OH:25])=[O:22])(=[O:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 86697512tert-Butyl [2-(6-acetyl-4-chloro-2-formyl-3-methylphenoxy)ethyl]carbamate

Produkt 1

HCID 866975173-Acetyl-2-{2-[(tert-butoxycarbonyl)amino]ethoxy}-5-chloro-6-methylbenzoic acidAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 31294Carbamide PeroxideLösungsmittel2×

Versuchsvorschrift

tert-Butyl [2-(6-acetyl-4-chloro-2-formyl-3-methylphenoxy)ethyl]carbamate (85 mg, 0.24 mmol) was stirred in methanol (7 mL) and 1.0 M sodium hydroxide in water (2.7 mL) and urea hydrogen peroxide addition compound (200 mg, 2 mmol) was added. Additional urea hydrogen peroxide addition compound (20 mg) and 1.0 M sodium hydroxide in water (0.5 mL) were added and the mixture was stirred for 3 more hours. 1 N HCl was added to pH 5 and the methanol was evaporated. The mixture was extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered and evaporated to give the desired compound (75 mg, 84%). LCMS calculated for C17H22ClNO6Na (M+Na)+: m/z=394.1; found: 393.9.

Aufarbeitung

  1. additionwas added
  2. additionwere added
  3. customthe methanol was evaporated
  4. extractionThe mixture was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-31dbbc89fc6b4db3ba645a35cef5762c
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309251B2

Notizen zur Reaktion

Wird geladen…