tert-Butyl (4-methoxy-2-methylphenyl)carbamate → 1-(2-(Tert-butoxycarbonylamino)-5-methoxyphenyl]-2-butanone

HRID 566683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 566683
C([Li])(CC)C.C1CCCCC1.[C:12]([O:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1[CH3:28])=[O:18])([CH3:15])([CH3:14])[CH3:13].CON(C)[C:32](=[O:35])[CH2:33][CH3:34]>C1COCC1>[C:12]([O:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1[CH2:28][C:32](=[O:35])[CH2:33][CH3:34])=[O:18])([CH3:15])([CH3:14])[CH3:13]

Komponenten

5

Edukt 3

HCID 10609919tert-Butyl (4-methoxy-2-methylphenyl)carbamateHCID 11344007N-Methoxy-N-methylpropionamideHCID 178418403HCID 178418403, Verbindung

Produkt 1

HCID 105178251-(2-(Tert-butoxycarbonylamino)-5-methoxyphenyl]-2-butanoneAusbeute 74,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

A solution of 1.3M sec-butyl lithium/cyclohexane (81 mL, 0.105 mol) was added slowly to 11.85 g (0.05 mol) of N-tert-butoxycarbonyl-4-methoxy-2-methylaniline in 80 mL of THF while keeping the temperature below −40° C. with a dry ice-ethanol bath. The bath was removed and the temperature allowed to rise to −20° C. and then the bath was replaced. After the temperature had cooled to −60° C., 6.1 g (0.052 mol) of N-methoxy-N-methylpropanamide in an equal volulme of THF was added dropwise. The reaction mixture was stirred 1 hour, the cooling bath removed and stirred an additional 1 hour. It was then poured into a mixture of 200 mL of ether and 200 mL of 1N HCl. The organic layer was separated, washed with water, dried over Na2SO4 and concentrated at reduced pressure to give 10.9 g (74% yield) of 1-(2-(tert-butoxycarbonylamino)-5-methoxyphenyl]-2-butanone, melting at 80-81° C., after chromatography on silica eluting with 5% EtOAc/toluene.

Aufarbeitung

  1. customthe temperature below −40° C.
  2. customThe bath was removed
  3. customto rise to −20° C.
  4. customthe cooling bath removed
  5. stirringstirred an additional 1 hour
  6. additionIt was then poured into a mixture of 200 mL of ether and 200 mL of 1N HCl
  7. customThe organic layer was separated
  8. washwashed with water
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-25bcc8cd13ba411bbddb01067f3218cc
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06175021B1

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