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

HRID 927400ノート

反応式

HRID 927400 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-f8659ae43c7849d7ae57cc64f90bea96
出典データセット
uspto-grants-2016_03
特許番号
US09290451B2

反応ノート

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