4-Toluenesulfonyl chloride → HCID 59563509, compound

HRID 1639512Notes

Reaction equation

HRID 1639512 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([C:8]2[O:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:11][N:12]=2)=[O:7])[CH2:3]1.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>>[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O:1][CH:2]2[CH2:5][N:4]([C:6]([C:8]3[O:9][C:10]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)=[N:11][N:12]=3)=[O:7])[CH2:3]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 58043098(3-Hydroxyazetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

Product 1

HCID 59563509HCID 59563509, compoundYield 90%

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).

Sources & evidence

ORD record
ord-154b4549900e4b0dbdc8e60f523b9864
Source dataset
uspto-grants-2012_02
Patent number
US08110566B2

Reaction notes

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