Water → HCID 22284650, compound
Reaction equation
[CH:1]([CH:4]1[C:9](=[O:10])[NH:8][CH:7]=[CH:6][S:5]1)([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:14][C:15]([O:17][CH3:18])=[O:16].O>O1CCCC1>[CH:1]([CH:4]1[C:9](=[O:10])[N:8]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:7]=[CH:6][S:5]1)([CH3:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (2RS)-2-isopropyl-3,4-dihydro-2H-1,4-thiazin-3-one (70 mg, Reference compound No. 42-1) in anhydrous tetrahydrofuran (1 ml) is added to a solution of sodium hydride (39 mg) in anhydrous tetrahydrofuran (1 ml) under ice cooling, and the mixture is stirred for 10 minutes. Methyl bromoacetate (74.3 mg) is added to the mixture, the temperature is raised to room temperature, and the whole is stirred for 20 minutes. The reaction mixture is cooled with ice, water is added to the mixture, and the whole is extracted with ethyl acetate. The extract is washed with 1 N hydrochloric acid, water and saturated brine successively and dried over anhydrous magnesium sulfate. The extract is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give the titled reference compound (90.2 mg).
Workup
- stirringthe whole is stirred for 20 minutes
- additionis added to the mixture
- extractionthe whole is extracted with ethyl acetate
- washThe extract is washed with 1 N hydrochloric acid, water and saturated brine successively
- dry with materialdried over anhydrous magnesium sulfate
- concentrationThe extract is concentrated under reduced pressure
- customthe resulting residue is purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-6b9350f6b6834b37bd671f3f063c724d
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06960575B2
Reaction notes
Loading…