Acetyl chloride → (ACETYLOXY)-CARBAMIC ACID TERT-BUTYL ESTER
Reaction equation
[OH:1][NH:2][C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C.[C:17](Cl)(=[O:19])[CH3:18]>ClCCl>[C:17]([O:1][NH:2][C:3]([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:9])(=[O:19])[CH3:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The starting material is prepared as follows: tert-Butyl N-hydroxycarbamate (3.89 g, 29.2 mmol) is dissolved in 25 ml of dichloromethane and cooled to 0° C. To this is added triethylamine (3.25 g, 32.1 mmol) and acetyl chloride (2.29 g, 29.2 mmol) dropwise. The mixture is extracted with ether and the extracts are washed with aqueous 2N HCl, water, 10% sodium bicarbonate, water, dried (MgSO4) and evaporated. The resulting colorless oil is purified by silica gel chromatography (10% ethyl acetate/hexane) to give O-acetyl-N-tert-butoxycarbonylhydroxylamine as a colorless oil.
Workup
- customThe starting material is prepared
- extractionThe mixture is extracted with ether
- washthe extracts are washed with aqueous 2N HCl, water, 10% sodium bicarbonate, water
- dry with materialdried (MgSO4)
- customevaporated
- customThe resulting colorless oil is purified by silica gel chromatography (10% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-0ec37788ff9f44f5826a6fdd931eb830
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05155130
Reaction notes
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