Acetyl chloride → tert-Butyl (2-acetamidoethyl)carbamate
Reaction equation
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][NH2:10])([CH3:4])([CH3:3])[CH3:2].[C:12](Cl)(=[O:14])[CH3:13]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][NH:10][C:12](=[O:14])[CH3:13])([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (2-amino-ethyl)-carbamic acid tert-butyl ester (1 eq.) in DCM was added TEA (3 eq.). The reaction was cooled to 0° C. Acetyl chloride (1 eq.) was filtered through a pad of alumina then added dropwise in solution in DCM to the reaction at 0° C. The reaction was stirred at 20° C. for 4 h. The crude was diluted with DCM, washed twice with water, then twice with a saturated aqueous solution of NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to afford (2-acetylamino-ethyl)-carbamic acid tert-butyl ester. The compound was used as such without further purification.
Workup
- washwashed twice with water
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-6bcea39ce54c43bbb3660b025f9353be
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759334B2
Reaction notes
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