Ammonium Chloride → N-[(1S,2R)-2-(3-Amino-4-benzyloxyphenyl)-2-hydroxy-1-methylethyl]-2,2,2-trifluoroacetamide

HRID 2220597노트

반응식

HRID 2220597 반응식
[Cl-].[NH4+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C@@H:17]([OH:27])[C@@H:18]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH3:19])=[CH:13][C:12]=1[N+:28]([O-])=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O.C(O)C.[Zn]>[NH2:28][C:12]1[CH:13]=[C:14]([C@@H:17]([OH:27])[C@@H:18]([NH:20][C:21](=[O:26])[C:22]([F:23])([F:24])[F:25])[CH3:19])[CH:15]=[CH:16][C:11]=1[O:10][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 86611766N-[(1S,2R)-2-(4-Benzyloxy-3-nitrophenyl)-2-hydroxy-1-methylethyl]-2,2,2-trifluoroacetamide

생성물 1

HCID 86611767N-[(1S,2R)-2-(3-Amino-4-benzyloxyphenyl)-2-hydroxy-1-methylethyl]-2,2,2-trifluoroacetamide수율 91.8%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

A solution of ammonium chloride (29 g) in water (133 mL) was added to a solution of N-[(1S,2R)-2-(4-benzyloxy-3-nitrophenyl)-2-hydroxy-1-methylethyl]-2,2,2-trifluoroacetamide (73 g) in ethanol (487 mL) at room temperature with stirring. The mixture was cooled with an ice, and then zinc powder (95 g) was added to the mixture with stirring over 10 minutes. The gray suspension was heated up to 70° C. over 15 minutes, and stirred at that temperature for 1 hr. The insoluble materials were removed by filtration, and the filtrate was concentrated in vacuo. Ethyl acetate and water were added to the residue, and the insoluble materials were removed by filtration again. The organic layer in the filtrate was separated, washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford the title compound (62 g).

후처리

  1. stirringwith stirring over 10 minutes
  2. stirringstirred at that temperature for 1 hr
  3. customThe insoluble materials were removed by filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionEthyl acetate and water were added to the residue
  6. customthe insoluble materials were removed by filtration again
  7. customThe organic layer in the filtrate was separated
  8. washwashed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-6b4d8f95f6a04d698524a8215c962770
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417169B2

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