tert-Butyl mercaptan → Tert-butyl (2-(tert-butyldisulfanyl)ethyl)carbamate

Temperature

-78 °C

1-Chloro-1H-benzo[d][1,2,3]triazole (1.73 g, 11.28 mmol) and 1H-benzo[d][1,2,3]triazole (0.67 g, 5.64 mmol) were dissolved in DCM (24.0 ml) under a nitrogen atmosphere, the mixture was cooled to −78° C., and a solution of tert-butyl(2-mercaptoethyl)carbamate (Compound 6a) (1.00 g, 5.64 mmol) in DCM (3.0 ml) was added dropwise. Following stirring at 78° C. for 10 minutes, a suspension of thiourea (1.29 g, 16.92 mmol) in THF (6.0 ml) was added and the mixture was further stirred for 10 minutes. A solution of 2-methylpropane-2-thiol (0.76 g, 8.46 mmol) in DCM (3.0 ml) was then added dropwise, and the mixture was stirred with warming to room temperature for 20 hours. The solid in the reaction solution was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (hexane:ethyl acetate=4:1) to afford the title compound (1.15 g, 77%).

1. additionwas added
2. stirringthe mixture was further stirred for 10 minutes
3. stirringthe mixture was stirred
4. temperaturewith warming to room temperature for 20 hours
5. customThe solid in the reaction solution was removed by filtration
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe residue was purified by column chromatography (hexane:ethyl acetate=4:1)

ORD record

ord-95b7bb491c5e4265ab91799331297610

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409952B2