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

HRID 2220597ノート

反応式

HRID 2220597 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6b4d8f95f6a04d698524a8215c962770
出典データセット
uspto-grants-2008_08
特許番号
US07417169B2

反応ノート

読み込み中…