Trifluoroacetic acid → HCID 58119712, compound

HRID 2368637Notes

Reaction equation

HRID 2368637 reaction equation
C[O:2][C:3](=O)[C:4]([C:11]#[N:12])=[CH:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.FC(F)(F)C(O)=O.[NH2:21][C:22]1[CH2:27][C:26]([CH3:29])([CH3:28])[CH2:25][C:24](=[O:30])[CH:23]=1>C(#N)C>[CH:6]1([CH:5]2[C:23]3[C:24](=[O:30])[CH2:25][C:26]([CH3:29])([CH3:28])[CH2:27][C:22]=3[NH:21][C:3](=[O:2])[CH:4]2[C:11]#[N:12])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 1366803-Amino-5,5-dimethyl-2-cyclohexen-1-oneHCID 66863338HCID 66863338, compound

Product 1

HCID 58119712HCID 58119712, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

13.3 g 2-Cyano-3-cyclopentyl-acrylic acid methyl ester and 5.8 ml trifluoroacetic acid are dissolved in 70 ml acetonitrile and heated for 7 days to reflux. During the first 5 days 3-amino-5,5-dimethyl-cyclohex-2-enone is added in daily portions (12 g in total). Afterwards the reaction mixture is cooled to 0° C., the precipitate is isolated by filtration, washed 2 times with cold acetonitrile and dried in vacuo. The product is obtained as a mixture of diastereomers.

Workup

  1. temperatureheated for 7 days
  2. temperatureto reflux
  3. customthe precipitate is isolated by filtration
  4. washwashed 2 times with cold acetonitrile
  5. customdried in vacuo
  6. customThe product is obtained as a mixture of diastereomers

Sources & evidence

ORD record
ord-5c5b9b5299b4467496a281d0e768a7f9
Source dataset
uspto-grants-2014_04
Patent number
US08703793B2

Reaction notes

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