反応 #1726684

反応方程式

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

収率 75.0%

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

収率 75.0%

溶媒

dichloromethane

反応条件

後処理

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

実験手順

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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