Acetic Acid → (S)-tert-Butyl 2-cyclopropyl-1-(5-methyl-1,2,4-oxadiazol-3-yl)ethylcarbamate

HRID 632029Notes

Reaction equation

HRID 632029 reaction equation
[C:1](O)(=O)[CH3:2].[NH2:5]/[C:6](=[N:20]\[OH:21])/[C@@H:7]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:8][CH:9]1[CH2:11][CH2:10]1>CN(C=O)C>[CH:9]1([CH2:8][C@H:7]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:16])[CH3:17])[C:6]2[N:5]=[C:1]([CH3:2])[O:21][N:20]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 89262365tert-butyl N-[(1Z,2S)-1-amino-3-cyclopropyl-1-hydroxyiminopropan-2-yl]carbamate

Product 1

HCID 71087824(S)-tert-Butyl 2-cyclopropyl-1-(5-methyl-1,2,4-oxadiazol-3-yl)ethylcarbamateYield 62.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of acetic acid (0.224 g, 4 mmol) in DMF (5 mL) was added N,N′-carbonyldiimidazole (0.6 g, 4 mmol) and the mixture was stirred for 0.5 h at room temperature. (S,Z)-tert-butyl 1-amino-3-cyclopropyl-1-(hydroxyimino)propan-2-ylcarbamate (0.84 g, 3 mmol) was added and the mixture was heated to 120° C. and stirred for 4 h. After evaporation of solvents, the residue was purified by column chromatography (silica gel, 20 g, eluting with 10% ethyl acetate in petroleum ether) to give the title compound (0.5 g; 54%) as yellow solid; MS (EI): m/e 290.1 [M+Na]+.

Workup

  1. temperaturethe mixture was heated to 120° C.
  2. stirringstirred for 4 h
  3. customAfter evaporation of solvents
  4. customthe residue was purified by column chromatography (silica gel, 20 g, eluting with 10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-f793e6f64375416c946ee97a270b054d
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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