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

HRID 632014노트

반응식

HRID 632014 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-6ac30c7139384524875438fa7413eac5
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321727B2

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