Methanol → tert-butyl N-[2-(1,2,4-oxadiazol-3-yl)propan-2-yl]carbamate

HRID 927468Notes

Reaction equation

HRID 927468 reaction equation
[NH2:1]/[C:2](=[N:14]\[OH:15])/[C:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:5])[CH3:4].[CH2:16](OC(OCC)OCC)C.FC(F)(F)C(O)=O.CO>C(#N)C.O>[O:15]1[CH:16]=[N:1][C:2]([C:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])([CH3:5])[CH3:4])=[N:14]1

Participants

7

Reactant 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 31214Ethyl orthoformateHCID 61324195tert-butyl N-[1-(N'-hydroxycarbamimidoyl)-1-methylethyl]carbamate

Product 1

HCID 73357654tert-butyl N-[2-(1,2,4-oxadiazol-3-yl)propan-2-yl]carbamateYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (Z)-tert-butyl 1-amino-1-(hydroxyimino)-2-methylpropan-2-ylcarbamate (Example 33 b, 2 g, 9.2 mmol) in acetonitrile (10 mL) was added triethoxymethane (CAN 122-51-0, 4.8 mL) and trifluoroacetic acid (CAN 76-05-1, 0.1 mL). The mixture was heated to 50° C. and stirred overnight. The reaction mixture was added to methanol (10 mL) and water (10 mL). After evaporation of solvents, the residue was purified by column chromatography (silica gel, 60 g, eluting with 30% to 50% ethyl acetate in petroleum ether) to give the target product (0.668 g, 32%) MS (EI): m/e=250.1 [M+H]+.

Workup

  1. customAfter evaporation of solvents
  2. customthe residue was purified by column chromatography (silica gel, 60 g, eluting with 30% to 50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-487f9c0ca488478f92fa929f95992bd7
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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