p-Toluenesulfonic acid → HCID 9879759, compound

HRID 413904Notes

Reaction equation

HRID 413904 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8]([O:10][C:11](=[O:25])[CH:12]([CH2:16][C:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:13](=O)[CH3:14])[CH3:9].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C.CCOCC>[CH2:8]([O:10][C:11]([C:12]1[CH:16]=[C:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:13]=1[CH3:14])=[O:25])[CH3:9]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7965CyclohexylamineHCID 312893Ethyl 2-acetyl-4-oxo-4-phenylbutanoate

Product 1

HCID 9879759HCID 9879759, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Cyclohexylamine (5 mmol, 0.5 g), 3-oxo-2-(2-oxo-2-phenyl-ethyl)-butyric acid ethyl ester (5 mmol, 1.2 g) and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The resulting residue was resuspended in ether, then washed with water and brine. The organic layer was dried over MgSO4, and the solids were separated and the solvents removed under vacuum. Purification of the oil yielded the named product, 1H-NMR (CDCl3, ppm): 1.0 bm (2H), 1.23 t (3H), 1.6-1.7 bm (8H), 2.66 s (3H), 4.16 q (2H), 6.39 s (1H), and 7.25 bm (5H).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solids were separated
  6. customthe solvents removed under vacuum
  7. customPurification of the oil
  8. customyielded the named product, 1H-NMR (CDCl3, ppm): 1.0 bm (2H), 1.23 t (3H), 1.6-1.7 bm (8H), 2.66 s (3H), 4.16 q (2H), 6.39 s (1H), and 7.25 bm (5H)

Sources & evidence

ORD record
ord-2007747859254c3a9de56c9a9b15508b
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Reaction notes

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