Triethylamine → (S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methanesulfonyloxy-butyric acid methyl ester
Reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C@H:11]([OH:16])[C:12]([O:14][CH3:15])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[CH3:15][O:14][C:12](=[O:13])[C@@H:11]([O:16][S:25]([CH3:24])(=[O:27])=[O:26])[CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2.48 g (10.00 mmol) of methyl (S)-4-(tert-butyldimethylsilyloxy)-2-hydroxybutanoate (J. Am. Chem. Soc. 2005, 127, 1090) in 50 ml of dichloromethane was treated with 2.09 ml (15.00 mmol, 1.5 eq) of triethylamine and at 0° C. during 5 min with 0.82 ml (10.50 mmol, 1.051 eq) of methanesulfonyl chloride. After 1 h at 0° C. the reaction was partitioned between 10% aq. potassium dihydrogenphosphate solution/diethyl ether (×3), the organic phases were washed with sat. aq. sodium hydrogencarbonate solution (freshly prepared) and 10% aq. sodium chloride solution, dried over Na2SO4 and evaporated to give 2.91 g (89%) of the titled compound as yellow oil. MS: 327.1 (MH+).
Workup
- customAfter 1 h at 0° C. the reaction was partitioned between 10% aq. potassium dihydrogenphosphate solution/diethyl ether (×3)
- washthe organic phases were washed with sat. aq. sodium hydrogencarbonate solution (
- customfreshly prepared) and 10% aq. sodium chloride solution
- dry with materialdried over Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-3acafe85bfef43dabec9b10989913cd7
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445674B2
Reaction notes
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