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

HRID 2220597Notes

Reaction equation

HRID 2220597 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6b4d8f95f6a04d698524a8215c962770
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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