Dimethyl Sulfide → HCID 54383053, compound

HRID 1637426Notes

Reaction equation

[C:1]([O:7][C@H:8]1[C@@H:20]([O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[C@H:19]([O:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[C@@H:18]([CH2:35][O:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[O:17][C@@H:9]1[S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C1C=C(Cl)C=C(C(OO)=[O:51])C=1.CSC>C(Cl)Cl>[C:1]([O:7][C@H:8]1[C@@H:20]([O:21][C:22](=[O:27])[C:23]([CH3:24])([CH3:26])[CH3:25])[C@H:19]([O:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[C@@H:18]([CH2:35][O:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[O:17][C@@H:9]1[S:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:51])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: -15 °C

Procedure

To a solution of 36 (1.38 g, 2.27 mmol) in 65 mL of CH2Cl2 at -78° C. is added m-CPBA (612 mg, 64%, 2.27 mmol). The reaction mixture is allowed to warm to -15° C. and then quenched with dimethyl sulfide (1 mL, 13.6 mmol) and allowed to warm to room temperature. The reaction mixture is diluted with 50 mL of CH2Cl2, extracted with H2O (100 mL), saturated NaHCO3 (100 mL), saturated NaCl (100 mL), dried over Na2SO4, filtered, and concentrated to afford a white solid. The sulfoxide is purified using flash chromatography (30% EtOAc/hexane) to afford 1.07 g (76%) of the title compound 37 as a mixture of diastereomers: Rf 0.35 and 0.38 (30% EtOAc/hexane).

Workup

temperatureto warm to room temperature
extractionextracted with H2O (100 mL), saturated NaHCO3 (100 mL), saturated NaCl (100 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customto afford a white solid
customThe sulfoxide is purified

Sources & evidence

ORD record: ord-593db4b5fdc54ae0a9257c9dcd5131c3
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06040433

Reaction notes

Loading…