Reaction #2446080

Reaction equation

tert-butyl cyclohexyl(2-hydroxypropyl)carbamate

2,4,6-trimethyl-benzoyl chloride

→

1-((tert-butoxycarbonyl)(cyclohexyl)amino)propan-2-yl 2,4,6-trimethylbenzoate

Solvents

ethyl acetate

toluene

Conditions

Workup

1. 1
   OtherThe resultant reaction mixture
2. 2
   Washwashed with water and brine
3. 3
   DryingThe organic layer was dried over sodium sulphate
4. 4
   Concentrationconcentrated to dryness

Procedure

To a solution of tert-butyl cyclohexyl(2-hydroxypropyl)carbamate (1 g, 3.89 mmol) in dry toluene (10 ml), 2,4,6-trimethyl-benzoyl chloride (0.510 mL, 4.280 mmol) was added. The resultant reaction mixture was stirred at rt for 16 hours. The reaction mixture was diluted in ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulphate, and concentrated to dryness to obtain 1-((tert-butoxycarbonyl)(cyclohexyl)amino)propan-2-yl 2,4,6-trimethylbenzoate. Yield: 1 g (64.10%); LCMS: m/z=404.4 [M+H], RT=2.76 min, (Column: Y, Program: P1)

Source