Methyl Carbamate → Ethyl 2-(methoxycarbonylamino)-3-methylbut-2-enoate

HRID 1411396노트

반응식

HRID 1411396 반응식
[CH2:1]([O:3][C:4](=[O:10])[C:5](=O)[CH:6]([CH3:8])[CH3:7])[CH3:2].[C:11](=[O:15])([O:13][CH3:14])[NH2:12].CC1C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1>C1C=CC=CC=1>[CH3:14][O:13][C:11]([NH:12][C:5](=[C:6]([CH3:8])[CH3:7])[C:4]([O:3][CH2:1][CH3:2])=[O:10])=[O:15]

참가 물질

5

반응물 3

HCID 11722Methyl CarbamateHCID 88406Ethyl 3-methyl-2-oxobutyrateHCID 161440Pyridine 4-methylbenzene-1-sulfonate

생성물 1

HCID 11117085Ethyl 2-(methoxycarbonylamino)-3-methylbut-2-enoate

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

A benzene solution (90 mL) of ethyl-3-methyl-2-oxobutanoate (4.03 g, 28.0 mmol), methyl carbamate (2.098 g, 28.0 mmol) and pyridine 4-methylbenzenesulfonate (0.70 g, 2.80 mmol) was heated to reflux in a round bottom flask equipped with a Dean-Stark trap and reflux condenser. After 44 hours of heating the mixture was cooled and then partitioned between ethyl acetate (50 mL) and brine (50 mL). The organic phase was washed with brine (2×50 mL) then dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography on silica gel (ethyl acetate-hexanes) to provide the title compound as an off white crystalline solid (1.487 g, 26%).

후처리

  1. temperatureto reflux in a round bottom flask
  2. customequipped with a Dean-Stark trap
  3. temperaturereflux condenser
  4. temperatureAfter 44 hours of heating the mixture
  5. temperaturewas cooled
  6. custompartitioned between ethyl acetate (50 mL) and brine (50 mL)
  7. washThe organic phase was washed with brine (2×50 mL)
  8. dry with materialthen dried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by chromatography on silica gel (ethyl acetate-hexanes)

출처 및 근거

ORD 기록
ord-1f4fbea6feaf4fb0988e35d1703a06ce
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921514B2

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