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

HRID 927468노트

반응식

HRID 927468 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-487f9c0ca488478f92fa929f95992bd7
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290451B2

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