Réaction #1438307

Équation de réaction

p-toluenesulfonyl chloride

tert-butyl N-(2-hydroxyethyl)carbamate

triethylamine

trimethylammonium chloride

iso-hexane

→

sub-title compound

Rendement 66.1%

2-(tert-Butyloxycarbonylamino)ethyl tosylate

Rendement 66.1%

Solvants

ethyl acetate

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Filtrationthen filtered
2. 2
   Lavagewashing with dichloromethane (100 mL)
3. 3
   LavageThe filtrate was washed with 10% citric acid (3×100 mL) and brine (100 mL)
4. 4
   SéchageThe organic layer was dried with magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   ConcentrationThe filtrate was concentrated under reduced pressure
7. 7
   Autreto give an oil
8. 8
   workup.STIRRINGThe resultant slurry was stirred at room temperature for 17 hours
9. 9
   Filtrationfiltered
10. 10
    LavageThe collected solid was washed with iso-hexane (240 mL)

Mode opératoire

A solution of p-toluenesulfonyl chloride (28.40 g, 148 mmol) in dichloromethane (100 mL) was added dropwise over 30 minutes at 0° C. to a mixture of tert-butyl N-(2-hydroxyethyl)carbamate (20 g, 120 mmol), triethylamine (18.80 g, 186 mmol) and trimethylammonium chloride (1.18 g, 12.4 mmol) in dichloromethane (120 mL). The mixture was stirred at 0° C. for 1 hour then filtered, washing with dichloromethane (100 mL). The filtrate was washed with 10% citric acid (3×100 mL) and brine (100 mL). The organic layer was dried with magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure to give an oil. The oil was dissolved in ethyl acetate (40 mL) and then iso-hexane (160 mL) was added slowly. The resultant slurry was stirred at room temperature for 17 hours and then filtered. The collected solid was washed with iso-hexane (240 mL) to yield the sub-title compound as a colourless powder (25 g, 64%).

Source