Methanesulfonyl chloride → (S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-yl methanesulfonate
Reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([OH:29])[CH2:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:30][S:31](Cl)(=[O:33])=[O:32]>N1C=CC=CC=1>[CH3:30][S:31]([O:29][C@@H:10]([CH2:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])(=[O:33])=[O:32]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-ol (1 eq) in pyridine (0.5 M) at 0° C., was added MsCl (2 eq). The reaction was stirred at 0° C. for 1 h and quenched by H2O. The aqueous phase was extracted with DCM. The combined organic phases were washed with H2O, and the aqueous phase was back extracted with DCM. The combined organic phases were washed with saturated NaHCO3 and brine, dried over anhydrous Na2SO4 and concentrated en vaccuo. The resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-15% EtOAc/Hex to give (S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-yl methanesulfonate as a colorless oil.
Workup
- customquenched by H2O
- extractionThe aqueous phase was extracted with DCM
- washThe combined organic phases were washed with H2O
- extractionthe aqueous phase was back extracted with DCM
- washThe combined organic phases were washed with saturated NaHCO3 and brine
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated en vaccuo
- customThe resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO)
Sources & evidence
- ORD record
- ord-3b0dcb9a884d4a40b4f722d83648ff2d
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08808703B2
Reaction notes
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