Acetic Acid → tert-Butyl 2-(5-methyl-1,2,4-oxadiazol-3-yl)propan-2-ylcarbamate

HRID 927400Notes

Reaction equation

HRID 927400 reaction equation
[C:1](O)(=O)[CH3:2].[NH2:5]/[C:6](=[N:18]\[OH:19])/[C:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:9])[CH3:8]>CN(C=O)C>[CH3:1][C:2]1[O:19][N:18]=[C:6]([C:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])([CH3:9])[CH3:8])[N:5]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 61324195tert-butyl N-[1-(N'-hydroxycarbamimidoyl)-1-methylethyl]carbamate

Product 1

HCID 71113127tert-Butyl 2-(5-methyl-1,2,4-oxadiazol-3-yl)propan-2-ylcarbamateYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of acetic acid (1.8 g) in DMF (50 mL) was added N,N′-carbonyldiimidazole (CAN 530-62-1, 4.865 g, mmol). The solution was stirred at ambient temperature for 0.5 h. (Z)-tert-butyl 1-amino-1-(hydroxyimino)-2-methylpropan-2-ylcarbamate (6.07 g) was added and the reaction mixture was stirred at 120° C. for 10 h. Removal of the solvent under reduced pressure left a yellow oil which was purified by column chromatography (silica gel 120 g, eluting with 30% ethyl acetate in petroleum ether) to give the title compound (5.38 g, 80%) as colorless oil; MS: m/e=264.1 [M+Na]+.

Workup

  1. additionwas added
  2. customRemoval of the solvent under reduced pressure
  3. waitleft a yellow oil which
  4. customwas purified by column chromatography (silica gel 120 g, eluting with 30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-f8659ae43c7849d7ae57cc64f90bea96
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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