m-Chloroperbenzoic acid → 4-Acetyl-2,3,4,5-tetrahydro-1,4-benzothiazepine 1-oxide
Reaction equation
[S:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][N:4]([C:12](=[O:14])[CH3:13])[CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:20]>ClCCl>[O:20]=[S:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][N:4]([C:12](=[O:14])[CH3:13])[CH2:3][CH2:2]1Participants
Procedure
To a cooled solution of 1-(2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)ethanone (70 g, 0.33 mol) in dichloromethane (700 mL) was added a solution of 3-chloroperoxybenzoic acid (67 g, 0.33 mol) in dichloromethane (800 mL) dropwise at 0° C. After the addition, the reaction was stirred at the same temperature for 15 minutes. The resulting reaction mixture was washed with a saturated aqueous solution of sodium carbonate (500 mL×2) and a saturated aqueous solution of sodium sulfite (500 mL×2). The combined aqueous layers were extracted with dichloromethane (200 mL×2), dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (eluting with 1-2% methanol in dichloromethane) to afford 57 g of the desired product (yield was 77%).
Workup
- additionAfter the addition
- customThe resulting reaction mixture
- washwas washed with a saturated aqueous solution of sodium carbonate (500 mL×2)
- extractionThe combined aqueous layers were extracted with dichloromethane (200 mL×2)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography (eluting with 1-2% methanol in dichloromethane)
Sources & evidence
- ORD record
- ord-a698b47151d04845add32927a2cc3e83
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871756B2
Reaction notes
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