Ammonium Acetate → N-(tert-Butyl)-2-amino-2-(4-fluorophenyl)ethanesulfonamide

HRID 72369

Reaction equation

HRID 72369 reaction equation
[C:1]([NH:5][S:6]([CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=O)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:25].[Na+]>CO>[C:1]([NH:5][S:6]([CH2:9][CH:10]([NH2:25])[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 68288463N-(tert-Butyl)-2-(4-fluorophenyl)-2-oxoethanesulfonamide

Product 1

HCID 68287917N-(tert-Butyl)-2-amino-2-(4-fluorophenyl)ethanesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.66 g of N-(tert-butyl)-2-(4-fluorophenyl)-2-oxoethanesulfonamide, 1.85 g of ammonium acetate and 0.17 g of sodium cyanoborohydride in 12 ml of methanol was stirred at 60° C. for 17 hours. After the removal of the solvent under reduced pressure, the residue was taken up in 50 ml of ethyl acetate and washed twice with 30 ml of 0.5 N aqueous sodium hydroxide solution and 30 ml of saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4 and concentrated by rotary evaporation. The crude product was subjected to a chiral separation.

Workup

  1. customAfter the removal of the solvent under reduced pressure
  2. washwashed twice with 30 ml of 0.5 N aqueous sodium hydroxide solution and 30 ml of saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated by rotary evaporation
  5. customThe crude product was subjected to a chiral separation

Sources & evidence

ORD record
ord-862b77b448334435a0c2e674fe13fedc
Source dataset
uspto-grants-2014_09
Patent number
US08828994B2

Linked notes

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