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

HRID 632082노트

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HRID 632082 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-264ec10aeb0f4f098f0f3ff478dea8d2
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321727B2

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