Water → tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamate
Reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21].O>C(Cl)Cl>[CH3:19][S:20]([O:1][CH2:2][CH2:3][NH:4][C:5]([O:6][C:7]([CH3:8])([CH3:10])[CH3:9])=[O:11])(=[O:22])=[O:21]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
tert-Butyl N-(2-hydroxyethyl)carbamate (6.0 g), triethylamine (5.68 ml) were dissolved in DCM (50 ml) and methanesulfonyl chloride (3.02 ml) was added dropwise to the reaction mixture at 0° C. The mixture was stirred for 30 min at 0° C. and stirring was continued for 2 h at RT. Water was added and the mixture was extracted with DCM. Combined organic phases were washed with water and brine, dried with Na2SO4 and evaporated. The product was stored under nitrogen. Yield 8.64 g. 1H-NMR (400 MHz; d6-DMSO): δ 1.39 (s, 9H), 3.16 (s, 3H), 3.23 (q, 2H), 4.16 (t, 2H), 7.04 (br s, 1H).
Workup
- stirringstirring
- waitwas continued for 2 h at RT
- extractionthe mixture was extracted with DCM
- washCombined organic phases were washed with water and brine
- dry with materialdried with Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-eda86f82f84c4342a79f10d54f0022e8
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975254B2
Reaction notes
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