Benzyl Bromide → N-[(1S,2R)-2-(4-Benzyloxy-3-nitrophenyl)-2-hydroxy-1-methylethyl]-2,2,2-trifluoroacetamide

HRID 2220596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2220596
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]([F:29])([F:28])[C:11]([NH:13][C@@H:14]([CH3:27])[C@H:15]([OH:26])[C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([N+:23]([O-:25])=[O:24])[CH:17]=1)=[O:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:22][C:19]1[CH:20]=[CH:21][C:16]([C@@H:15]([OH:26])[C@@H:14]([NH:13][C:11](=[O:12])[C:10]([F:29])([F:28])[F:9])[CH3:27])=[CH:17][C:18]=1[N+:23]([O-:25])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 866117642,2,2-Trifluoro-N-[(1S,2R)-2-hydroxy-2-(4-hydroxy-3-nitrophenyl)-1-methylethyl]acetamide

Produkt 1

HCID 86611766N-[(1S,2R)-2-(4-Benzyloxy-3-nitrophenyl)-2-hydroxy-1-methylethyl]-2,2,2-trifluoroacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Benzyl bromide (22 mL) was added to a suspension of 2,2,2-trifluoro-N-[(1S,2R)-2-hydroxy-2-(4-hydroxy-3-nitrophenyl)-1-methylethyl]acetamide (55 g) and potassium carbonate (36.8 g) in N,N-dimethylformamide (529 mL) at room temperature with stirring, and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was concentrated in vacuo, and ethyl acetate and water were added to the residue. The organic layer was separated, washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford the title compound (73 g).

Aufarbeitung

  1. stirringthe mixture was stirred at 60° C. for 1 hr
  2. concentrationThe reaction mixture was concentrated in vacuo, and ethyl acetate and water
  3. additionwere added to the residue
  4. customThe organic layer was separated
  5. washwashed successively with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-aa21642c4c644e2f9e459bb387fe40ee
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07417169B2

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