Potassium bisulfate → tert-butyl N-(3-oxobutyl)carbamate
Reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH2:9][C:10](=[O:15])NCOC)([CH3:4])([CH3:3])[CH3:2].[CH3:17][Mg+].[Br-].OS([O-])(=O)=O.[K+]>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH2:9][C:10](=[O:15])[CH3:17])([CH3:2])([CH3:3])[CH3:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
A solution of BOC-beta-alanine (20 g, 105 mmol), 10-2 (10.3 g, 105 mmol), BOP reagent (46.5 g, 105 mmol), and N-methylmorpholine (46 mL, 420 mmol) in acetonitrile (500 mL) was stirred for 15 h. The reaction was diluted with EtOAc, washed with H2O, 10% KHSO4(aq.), sat. NaHCO3, dried (MgSO4) and concentrated to give crude [2-(methoxymethyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester 10-3 as a yellow oil. TLC Rf=0.42 (silica, 20% EtOAc/hexanes). To a solution of this crude amide in THF (500 mL) at 0° C. was added CH3MgBr (100 mL of 3M in ether, 300 mmol) over 30 minutes. After 2 h, 10% KHSO4(aq.) was added, the mixture warmed to 25° C., and diluted with EtOAc. The organics were washed with sat. NaHCO3, dried (MgSO4) and concentrated. Flash chromatography (silica, 20% EtOAc/hexanes) gave 10-4 as a yellow oil.
Workup
- washThe organics were washed with sat. NaHCO3
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-45e09eee11084ce8a6665ba659ae4311
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06784190B2
Reaction notes
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