Ethyl Acetate → methanesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([C@H:13]1[C@@H:17]([CH2:18][OH:19])[O:16][C:15](=[O:20])[NH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([O-])(O)=O.[Na+].C(OCC)(=O)C>CC(C)=O.CN1CCOCC1>[CH2:6]([C@H:13]1[C@@H:17]([CH2:18][O:19][S:2]([CH3:1])(=[O:4])=[O:3])[O:16][C:15](=[O:20])[NH:14]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
A solution of 4.7 ml of methanesulphonyl chloride in 10 ml of acetone is added at 25° C. to a suspension of 10.4 g of the alcohol from Example 8 in 20 ml of acetone and 6.1 ml of N-methylmorpholine and the suspension is stirred at 25° C. for 3 hours. A further 1.1 ml of N-methylmorpholine are added and the mixture is stirred for 1 hour. The suspension is shaken with 80 ml of semi-saturated NaHCO3 solution and ethyl acetate and the separated aqueous phase is extracted with ethyl acetate. The ethyl acetate extracts are washed with water, dried and filtered. The filtrate is concentrated to give 14.3 g (100%) of crude methanesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester, TLC (SiO2 ethyl acetate): Rf =0.4; MS (El): 286 (M+H+).
Workup
- stirringthe mixture is stirred for 1 hour
- extractionthe separated aqueous phase is extracted with ethyl acetate
- washThe ethyl acetate extracts are washed with water
- customdried
- filtrationfiltered
- concentrationThe filtrate is concentrated
Sources & evidence
- ORD record
- ord-873717bc59254a57b7060d047ff404ed
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05919949
Reaction notes
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