Dimethyl Sulfide → HCID 10555910, compound
Reaction equation
[C:1]1([S:7][C@@H:8]2[O:34][C@H:33]([CH2:35][O:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[C@@H:25]([O:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[C@H:17]([O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[C@H:9]2[O:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C(Cl)C=C(C(OO)=[O:51])C=1.CSC>C(Cl)Cl>[C:11]([O:10][C@@H:9]1[C@@H:17]([O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:21])[CH3:22])[C@H:25]([O:26][C:27](=[O:32])[C:28]([CH3:29])([CH3:30])[CH3:31])[C@@H:33]([CH2:35][O:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[O:34][C@H:8]1[S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:51])(=[O:16])[C:12]([CH3:13])([CH3:14])[CH3:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -15 °C
Procedure
To a solution of 44 (1.24 g, 2.04 mmol) in 25 mL of CH2Cl2 at -78° C. is added a solution of 64% m-CPBA (550 mg, 2.04 mmol) in 10 mL of CH2Cl2. The reaction mixture is allowed to warm to -15° C., quenched with methyl sulfide (2.07 mL, 1.75 g, 6.8 mmol) and warmed to room temperature. The reaction mixture is then diluted with 25 mL CH2Cl2, washed with saturated NaHCO3 (50 mL), H2O (50 mL), saturated NaCl (50 mL), dried over Na2SO4, filtered, concentrated and purified by flash chromatography (30% EtOAc/hexane) to afford 1.14 g (89%) of the title compound 45 as a mixture of diastereomers: Rf 0.14 and 0.28 (10% EtOAc/hexane).
Workup
- temperaturewarmed to room temperature
- washwashed with saturated NaHCO3 (50 mL), H2O (50 mL), saturated NaCl (50 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- custompurified by flash chromatography (30% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-64f966fdd262404c85171b51c4bda257
- Source dataset
- uspto-grants-2000_03
- Patent number
- US06040433
Reaction notes
Loading…