Dimethylacetoacetamide → tert-Butyl 2-(3-Methoxycarbonyladamant-1-ylcarbonylamino)-6-(N,N-dimethylaminocarbonyl)hex-4-ynoate

HRID 1242839

반응식

HRID 1242839 반응식
[CH3:1][O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][C:7]([C:15]([NH:17][CH:18]([CH2:26][C:27]#[CH:28])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])([CH2:8]3)[CH2:6]1)[CH2:12]2)=[O:4].[CH3:29][N:30]([CH3:37])[C:31](=[O:36])[CH2:32]C(C)=O>C1C=CC=CC=1.[O-]S([O-])(=O)=O.[Cu+2]>[CH3:1][O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][C:7]([C:15]([NH:17][CH:18]([CH2:26][C:27]#[C:28][CH2:32][C:31]([N:30]([CH3:37])[CH3:29])=[O:36])[C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])=[O:16])([CH2:8]3)[CH2:6]1)[CH2:12]2)=[O:4]

참가 물질

5

반응물 2

HCID 16278DimethylacetoacetamideHCID 21940505tert-Butyl 2-(3-methoxycarbonyladamant-1-ylcarbonylamino)pent-4-ynoate

생성물 1

HCID 21940554tert-Butyl 2-(3-Methoxycarbonyladamant-1-ylcarbonylamino)-6-(N,N-dimethylaminocarbonyl)hex-4-ynoate

시약·촉매·용매 2

HCID 24462Copper Sulfate촉매HCID 241Benzene용매

실험 절차

tert-Butyl 2-(3-methoxycarbonyladamant-1-ylcarbonylamino)pent-4-ynoate (0.44 g) was dissolved in 0.8 mL of dry benzene under nitrogen. To this solution was added a catalytic amount of CuSO4 and the reaction mixture was brought to reflux. N,N-Dimethyl acetoacetamide was added dropwise in excess. Evolution of nitrogen was observed. The addition was complete after 30 min. The reaction was then heated for another 30 min. After cooling the reaction mixture, the solvent was evaporated under reduced pressure and the crude product was purified on a prep plate (silica gel; EtOAc/hexanes, 2:3) to afford the title compound as an oil.

후처리

  1. temperatureto reflux
  2. additionThe addition
  3. temperatureThe reaction was then heated for another 30 min
  4. temperatureAfter cooling the reaction mixture
  5. customthe solvent was evaporated under reduced pressure
  6. customthe crude product was purified on a prep plate (silica gel; EtOAc/hexanes, 2:3)

출처 및 근거

ORD 기록
ord-9ee51b8828e64373a76bf75068b9ca6f
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115768B2

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