Dimethyl Sulfide → HCID 15172752, compound

Temperature

0 °C

To a solution of alcohol E (1.0 g, 3.1 mmol) and methyl sulfide (1.8 mL, 24.8 mmol) in acetonitrile (31 mL) at 0° C. was added benzoyl peroxide (3.0 g, 12.4 mmol) in four equal portions over 10 min, and the mixture was stirred at 0° C. for 1 h and then at room temperature for 1 h until no E was observed by TLC. The mixture was diluted with ethyl acetate (100 mL), washed with 10% Na2CO3 (100 mL) and then brine (100 mL) and dried over sodium sulfate. The solvent was removed in vacuo to give crude product which was used for the next step without purification. The resulting residue was dissolved in acetonitrile (10 mL) and followed by addition of diethyl amine (6.2 mL, 60 mmol). The mixture was stirred at room temperature for overnight until no starting material was observed by TLC and concentrated in vacuo. The residue was flash chromatographed on silica gel with 5% MeOH/DCM to provide intermediate H (270 mg, yield 54% over two steps). MS (ESI) m/z 162.83 (M+H)+.

1. waitat room temperature for 1 h until no E was observed by TLC
2. washwashed with 10% Na2CO3 (100 mL)
3. dry with materialbrine (100 mL) and dried over sodium sulfate
4. customThe solvent was removed in vacuo
5. customto give crude product which
6. customwas used for the next step without purification
7. dissolutionThe resulting residue was dissolved in acetonitrile (10 mL)
8. stirringThe mixture was stirred at room temperature for overnight until no starting material
9. concentrationconcentrated in vacuo
10. customchromatographed on silica gel with 5% MeOH/DCM

ORD record

ord-0c9f630d072345d293387b1aad811185

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096625B2