4-(Tert-butyldimethylsilyloxy)methylbenzhydrazide → 2-(4-(((Tert-butyldimethylsilyl)oxy)methyl)phenyl)-5-cyclopropyl-1,3,4-oxadiazole

HRID 1798603Notes

Reaction equation

HRID 1798603 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([NH:16][NH2:17])=[O:15])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.[CH:21]1([C:24](=N)OCC)[CH2:23][CH2:22]1>>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]2[O:15][C:24]([CH:21]3[CH2:23][CH2:22]3)=[N:17][N:16]=2)=[CH:18][CH:19]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 107079144-(Tert-butyldimethylsilyloxy)methylbenzhydrazideHCID 20026660Ethyl cyclopropanecarboximidate hydrochloride

Product 1

HCID 584320052-(4-(((Tert-butyldimethylsilyl)oxy)methyl)phenyl)-5-cyclopropyl-1,3,4-oxadiazoleYield 40%

Procedure

4-(((Tert-butyldimethylsilyl)oxy)methyl)benzohydrazide was reacted with ethyl cyclopropanecarbimidate hydrochloride according to the procedure used for the synthesis of Example 18. Purification by chromatography (EtOAc-hexanes) gave 2-(4-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)-5-cyclopropyl-1,3,4-oxadiazole as a brown oil (3.7 g, 40% yield).

Workup

  1. customused for the synthesis of Example 18
  2. customPurification by chromatography (EtOAc-hexanes)

Sources & evidence

ORD record
ord-d0670a1bc12a4353aa35864724de55a4
Source dataset
uspto-grants-2013_01
Patent number
US08343970B2

Reaction notes

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