Sodium Sulfite → HCID 10309658, compound
Reaction equation
[O:1]=[S:2]1(=[O:26])[CH2:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][C:9]=2[F:25])[CH2:4][CH2:3]1.CS(N)(=O)=[O:29].S([O-])([O-])=O.[Na+].[Na+]>C(O)(C)(C)C.O>[OH:29][C:5]1([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][C:9]=2[F:25])[CH:4]=[CH:3][S:2](=[O:1])(=[O:26])[CH2:7][CH2:6]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of (S)-N-[[3-[4-(3,6-dihydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (0.415 g, 1.08 mmol; prepared as described in U.S. Pat. No. 5,968,962) in 1:1 t-butanol-water (4 mL) is added to a solution of the standard reagent AD mix-β (1.51 g; available from Aldrich Co.) and methanesulfonamide (0.103 g, 1.08 mmol) in 1:1 t-butanol-water (10 mL) cooled at 0° C. The reaction mixture is stirred 5 days at 4° C. and then treated with sodium sulfite (1.5 g) and stirred 30 minutes. The solution is then extracted with four 10 mL portions of ethyl acetate and the combined organic phases dried (MgSO4), filtered and concentrated. Purification by column chromatography (0-5% MeOH-DCM) provided the title compound as a mixture of diastereomers. Yield 0.29 g (64%). 1H NMR.
Workup
- customprepared
- stirringstirred 30 minutes
- extractionThe solution is then extracted with four 10 mL portions of ethyl acetate
- dry with materialthe combined organic phases dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customPurification by column chromatography (0-5% MeOH-DCM)
Sources & evidence
- ORD record
- ord-736e404c78f74c7d8b31a342cd1c5974
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06884813B2
Reaction notes
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