Reacción #1726690

Ecuación de reacción

4A

(3-Hydroxyazetidin-1-yl)(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone

Triethylamine

methanesulfonyl chloride

→

4B

Rendimiento 177.9%

1-(5-(4-Methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl methanesulfonate

Rendimiento 177.9%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas cooled in an ice-bath
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Otrothe cooling bath was removed
4. 4
   OtroThe mixture was transferred to a separatory funnel
5. 5
   Lavadowas washed with water
6. 6
   OtroThe organic solution was dried (phase separator)
7. 7
   Otroevaporated
8. 8
   workup.ADDITIONDichloromethane (50 mL) and diethyl ether (200 mL) were added
9. 9
   Filtraciónthe solid product was filtered
10. 10
    LavadoThe product was washed twice with diethyl ether
11. 11
    Otrodried in vacuo

Procedimiento

A suspension of 4A (5.45 g, 19. 8 mmol) in dichloromethane (100 mL) was cooled in an ice-bath. Triethylamine (4.4 mL, 31.7 mmol) was added followed by methanesulfonyl chloride (2.3 mL, 29.7 mmol). After the addition, the cooling bath was removed. The mixture was stirred for 7 h. The mixture was transferred to a separatory funnel and was washed with water followed by aqueous NaHCO3 (sat.). The organic solution was dried (phase separator) and evaporated. Dichloromethane (50 mL) and diethyl ether (200 mL) were added and the solid product was filtered. The product was washed twice with diethyl ether and then dried in vacuo. There was obtained 5.03 g (72%) of 4B as a solid. 1H NMR (500 MHz, CDCl3): δ 3.13 (s, 3H), 3.90 (s, 3H), 4.42 (dd, 1H), 4.64 (dd, 1H), 4.86 (dd, 1H), 5.11 (dd, 1H), 5.40 (m, 1H), 7.02 (d, 2H), 8.09 (d, 2H), MS (APCI+) m/z 354 [M+H]+.

Fuente