m-Chloroperbenzoic acid → HCID 15460414, compound
Reaction equation
[N:1]([C@H:4]1[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:15]([O:21][C:22](=[O:24])[CH3:23])[C@H:14]([CH3:25])[O:13][CH:5]1[S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+:2]=[N-:3].C([O-])(O)=[O:27].[Na+].C1C=C(Cl)C=C(C(OO)=O)C=1>C(Cl)Cl>[N:1]([C@H:4]1[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:15]([O:21][C:22](=[O:24])[CH3:23])[C@H:14]([CH3:25])[O:13][CH:5]1[S:6]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:27])=[N+:2]=[N-:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of phenyl 2-azido-3,4-di-O-acetyl-2,6-dideoxy-1-thio-L-galactopyranoside (22) (1.02 g, 2.80 mmol) in 50 mL of CH2Cl2 is added NaHCO3 at room temperature. The reaction mixture is cooled to -78° C., and mCPBA (0.878 g, 2.80 mmol, 50-60%) is added. The reaction mixture is stirred at -78° C. for 30 minutes and then allowed to warm to -40° C. over 1 h. The reaction is quenched with dimethyl sulfide (1 mL) at -40° C. and then poured into a solution of saturated NaHCO3 (50 mL) and extracted with CH2Cl2 (3×30 mL) The organic layers are combined, dried over Na2SO4, filtered, concentrated, and purified by flash chromatography (EtOAc/petroleum ether) to afford the title compound 26 as a mixture of diastereomers.
Workup
- temperatureto warm to -40° C. over 1 h
- customThe reaction is quenched with dimethyl sulfide (1 mL) at -40° C.
- additionpoured into a solution of saturated NaHCO3 (50 mL)
- extractionextracted with CH2Cl2 (3×30 mL) The organic layers
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- custompurified by flash chromatography (EtOAc/petroleum ether)
Sources & evidence
- ORD record
- ord-94f756c4be4541d98d3a9f0f1781f59a
- Source dataset
- uspto-grants-2000_03
- Patent number
- US06040433
Reaction notes
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