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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1774655Generated: November 2, 2026

4-Toluenesulfonyl chloride → 2-(tert-Butoxycarbonyl(methyl)amino)-ethyl 4-methylbenzenesulfonate

https://huagongshe.com/reaction/1774655

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Toluenesulfonyl chlorideHCID 7397—
ReactantTriethylamineHCID 8471—
ReactantN-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanolHCID 545700—
SolventDichloromethaneHCID 6344—
Product2-(tert-Butoxycarbonyl(methyl)amino)-ethyl 4-methylbenzenesulfonateHCID 2158115661%

Reaction Steps

To a mixture of 112a (9.0 g, 51 mmol), and Et3N (18.6 mL, 51 mmol) in DCM (100 mL) was added TsCl (9.77 g, 51 mmol). The mixture was stirred at rt for 4 h and concentrated. The residue was diluted with EA, washed with water. The organic layer was dried and concentrated to give 2-(tert-butoxycarbonyl(methyl)amino)ethyl 4-methylbenzenesulfonate 112b (10.0 g, 61%) as light yellow oil. ESI-LCMS: m/z=230.0

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09260415B2
Source datasetuspto-grants-2016_02
ORD IDord-b07a8d8a777041a68e7f3c4dec6599b4
Source noteuspto-grants-2016_02