proline dl-form → HCID 58119762, compound

HRID 2368641Notes

Reaction equation

HRID 2368641 reaction equation
[NH2:1][C:2]([CH:16]([O:18][CH3:19])[CH3:17])=[CH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)=[O:5].[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1.[CH3:29][C:30]1([CH3:38])[CH2:35][C:34](=[O:36])[CH2:33][C:32](=O)[CH2:31]1.N1CCCC1C(O)=O>C(O)C>[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]2[C:33]3[C:34](=[O:36])[CH2:35][C:30]([CH3:38])([CH3:29])[CH2:31][C:32]=3[NH:1][C:2]([CH:16]([O:18][CH3:19])[CH3:17])=[C:3]2[C:4](=[O:5])[C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:14])([F:15])[F:13])=[CH:8][CH:7]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 614proline dl-formHCID 31358DimedoneHCID 680234-FluorobenzaldehydeHCID 66862226HCID 66862226, compound

Product 1

HCID 58119762HCID 58119762, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.4 g 3-Amino-4-methoxy-1-(4-trifluoromethyl-phenyl)-pent-2-en-1-one are dissolved in 25 ml of ethanol, 2.51 ml 4-fluorobenzaldehyde and 3.28 g 5,5-dimethyl-cyclohexane-1,3-dione and 270 mg DL-proline are successively added and the mixture is stirred for 30 minutes at room temperature. Then the mixture is heated for 24 hours to reflux at a dean-stark trap. After cooling to room temperature the solvents are evaporated in vacuo. The residue is chromatographed on silica gel.

Workup

  1. temperatureThen the mixture is heated for 24 hours
  2. temperatureto reflux at a dean-stark trap
  3. temperatureAfter cooling to room temperature the solvents
  4. customare evaporated in vacuo
  5. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-601996bd09ea4ea2b052d01250dfd331
Source dataset
uspto-grants-2014_04
Patent number
US08703793B2

Reaction notes

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