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

HRID 1242839

反応式

HRID 1242839 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒HCID 241Benzene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9ee51b8828e64373a76bf75068b9ca6f
出典データセット
uspto-grants-2006_10
特許番号
US07115768B2

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