Reaction #1726694

Reaction equation

1B

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

4-methylbenzene-1-sulfonyl chloride

→

8B

Yield 90.0%

1-(5-Phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl 4-methylbenzenesulfonate

Yield 90.0%

Conditions

Procedure

Using a similar protocol as described in Example 2C but employing 1B (250 mg, 1.02 mmol) and 4-methylbenzene-1-sulfonyl chloride (250 mg, 1.31 mmol) as starting materials afforded 365 mg (90%) of 8B as a solid. 1H NMR (500 MHz, CDCl3): δ 2.49 (s, 3H), 4.24 (dd, 1H), 4.47 (dd, 1H), 4.72 (dd, 1H), 4.98 (dd, 1H), 5.22 (m, 1H), 7.41 (d, 2H), 7.53 (t, 2H), 7.59 (t, 1H), 7.82 (d, 2H), 8.14 (d, 2H).

Source