Реакция #1726684

Уравнение реакции

methanesulfonyl chloride

2B

(5-(4-Chlorophenyl)-1,3,4-oxadiazol-2-yl)(3-hydroxyazetidin-1-yl)methanone

methyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate

Triethylamine

→

2C

Выход 75.0%

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

Выход 75.0%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Температураwas cooled in an ice-bath
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Другоеthe cooling bath was removed
4. 4
   ДругоеThe reaction mixture was transferred to a reparatory funnel
5. 5
   Промывкаwas washed with water
6. 6
   ДругоеThe organic solution was dried (phase separator)
7. 7
   Другоеevaporated
8. 8
   workup.ADDITIONDichloromethane (50 mL) and diethyl ether (200 mL) were added
9. 9
   Фильтрацияthe solid product was collected by filtration
10. 10
    ПромывкаThe solid was washed twice with diethyl ether
11. 11
    Другоеdried in vacuo
12. 12
    ДругоеThe product was purified
13. 13
    Промывкаfirst eluting with dichloromethane
14. 14
    workup.ADDITIONwith a mixture of dichloromethane and methanol containing 2M NH3 (20:1)

Методика

A suspension of 2B —which contained approximately 50% of methyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate as an impurity—(1.38 g, 2.47 mmol) in dichloromethane (50 mL) was cooled in an ice-bath. Triethylamine (0.51 mL, 3.70 mmol) was added followed by methanesulfonyl chloride (0.27 mL, 3.45 mmol). After the addition, the cooling bath was removed. The mixture was stirred for 7 h. The reaction mixture was transferred to a reparatory funnel and was washed with water followed by aqueous NaHCO3. The organic solution was dried (phase separator) and evaporated. Dichloromethane (50 mL) and diethyl ether (200 mL) were added and the solid product was collected by filtration. The solid was washed twice with diethyl ether and then dried in vacuo. The product was purified using flash column chromatography first eluting with dichloromethane and then with a mixture of dichloromethane and methanol containing 2M NH3 (20:1). There was obtained 0.66 g (75%) of 2C as a solid. 1H NMR (500 MHz, CDCl3): δ 3.13 (s, 3H), 4.43 (dd, 1H), 4.65 (dd, 1H), 4.87 (dd, 1H), 5.12 (dd, 1H), 5.41 (m, 1H), 7.53 (d, 2H), 8.10 (d, 2H), MS (APCI+) m/z 358 [M+H]+.

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