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

HRID 2220596노트

반응식

HRID 2220596 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-aa21642c4c644e2f9e459bb387fe40ee
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417169B2

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