Réaction #1726694

ord-154b4549900e4b0dbdc8e60f523b9864

Équation de réaction

O=C(c1nnc(-c2ccccc2)o1)N1CC(O)C1
1B
O=C(c1nnc(-c2ccccc2)o1)N1CC(O)C1
(3-Hydroxyazetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone
Cc1ccc(S(=O)(=O)Cl)cc1
4-methylbenzene-1-sulfonyl chloride
Cc1ccc(S(=O)(=O)OC2CN(C(=O)c3nnc(-c4ccccc4)o3)C2)cc1
8B
Rendement 90.0%
Cc1ccc(S(=O)(=O)OC2CN(C(=O)c3nnc(-c4ccccc4)o3)C2)cc1
1-(5-Phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl 4-methylbenzenesulfonate
Rendement 90.0%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

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

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08110566B2uspto-grants-2012_02