tert-Butanol → tert-butyl N-(chlorosulfonyl)carbamate
Reaction equation
[O:1]=[C:2]=[N:3][S:4]([Cl:7])(=[O:6])=[O:5].[CH3:8][C:9]([OH:12])([CH3:11])[CH3:10].CCCCCC>C1C=CC=CC=1>[Cl:7][S:4]([NH:3][C:2](=[O:1])[O:12][C:9]([CH3:11])([CH3:10])[CH3:8])(=[O:6])=[O:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
N-(oxomethylene)sulfamoyl chloride (13.4 mmol) was dissolved in dry benzene (5 mL) and dropwise added t-BuOH (13.4 mmol) while the temperature was kept below 25° C. The reaction mixture was stirred at 25° C. for 2 h, added hexane (5 mL) and cooled to 0° C. Precipitate was collected by filtration, washed with hexane affording tert-butyl N-chlorosulfonylcarbamate as white crystals. 4-(4,7-diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine (4.6 mmol) (intermediate 21) was suspended in dry DCM (25 mL) and added triethylamine (6.9 mmol). To this suspension was slowly added tert-butyl N-chlorosulfonylcarbamate (4.6 mmol) at rt. After 15 min all starting material has been consumed. The obtained reaction mixture was concentrated in vacuo on celite. The product was purified by flash chromatography on silica using EtOAc:MeOH in heptane as eluent.
Workup
- customwas kept below 25° C
- temperaturecooled to 0° C
- filtrationPrecipitate was collected by filtration
- washwashed with hexane
Sources & evidence
- ORD record
- ord-adbc00b6728a4e0c93d71fadf89f3f15
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09233964B2
Reaction notes
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