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

HRID 991764Notes

Reaction equation

HRID 991764 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 241BenzeneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-c0ceabe7662e4efbbc3b31b9e99157dc
Source dataset
uspto-grants-2002_10
Patent number
US06465513B1

Reaction notes

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