Sodium hydride → 2-[N'-(tert-butoxycarbonyl)-2,2-difluoro-2-(3-butoxyphenyl)-ethylamino]-N,N-dimethyl-acetamide

HRID 62592

Reaktionsgleichung

Reaktionsgleichung von HRID 62592
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([F:23])([F:22])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:26][N:27]([CH3:32])[C:28](=[O:31])[CH2:29]Cl>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH2:9][C:10]([F:22])([F:23])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=1)[CH2:29][C:28]([N:27]([CH3:32])[CH3:26])=[O:31])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 758862-chloro-N,N-dimethylacetamideHCID 71153310N-(tert-butoxycarbonyl)-2,2-difluoro-2-(3-butoxyphenyl)ethylamine

Produkt 1

HCID 711521572-[N'-(tert-butoxycarbonyl)-2,2-difluoro-2-(3-butoxyphenyl)-ethylamino]-N,N-dimethyl-acetamideAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

150 mg (0.46 mmol) of N-(tert-butoxycarbonyl)-2,2-difluoro-2-(3-butoxyphenyl)ethylamine are dissolved in dry DMF (2.5 mL) and the solution was cooled to 0° C. NaH (60% in mineral oil; 22 mg; 0.55 mmol) is added and the reaction mixture stirred for 10 minutes at 0° C. and for further 10 minutes at room temperature. The reaction mixture is cooled again at 0° C., then N,N-dimethylchloroacetamide (73 mg; 0.60 mmol) is added and stirring is continued for 24 hours at room temperature. The reaction is quenched with water, extracted three times with EtAc, washed with brine. The organic phases are dried over anhydrous Na2SO4, filtered and evaporated. The residue is flash-chromatographed on silica gel (eluant: DCM/EtAc, from 98/2 to 95/5). 2-[N′-(tert-butoxycarbonyl)-2,2-difluoro-2-(3-butoxyphenyl)-ethylamino]-N,N-dimethyl-acetamide (165 mg; 87%) is obtained as a white solid.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled again at 0° C.
  2. stirringstirring
  3. waitis continued for 24 hours at room temperature
  4. customThe reaction is quenched with water
  5. extractionextracted three times with EtAc
  6. washwashed with brine
  7. dry with materialThe organic phases are dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is flash-chromatographed on silica gel (eluant: DCM/EtAc, from 98/2 to 95/5)

Quellen und Nachweise

ORD-Eintrag
ord-9db9639f05254c029aeabba26021386a
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447029B2

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