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

HRID 2220596Notes

Reaction equation

HRID 2220596 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-aa21642c4c644e2f9e459bb387fe40ee
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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