Dicyclohexylamine → HCID 13104429, compound

HRID 1758694Notes

Reaction equation

HRID 1758694 reaction equation
[CH2:1]1[S:5][CH2:4][NH:3][CH:2]1[C:6]([OH:8])=[O:7].C1(NC2CCCCC2)CCCCC1.O1CCOCC1.[C:28]([CH2:36][CH:37]([CH3:41])[C:38](O)=[O:39])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(#N)C>[C:28]([CH2:36][CH:37]([CH3:41])[C:38]([N:3]1[CH:2]([C:6]([OH:8])=[O:7])[CH2:1][S:5][CH2:4]1)=[O:39])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 7582DicyclohexylamineHCID 9934TimonacicHCID 312751,4-DioxaneHCID 744922-Methyl-4-oxo-4-phenylbutanoic acid

Product 1

HCID 13104429HCID 13104429, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.0 g. (0.015 mole) of L-thiazolidine-4-carboxylic acid and 2.72 g. (0.015 mole) of dicyclohexylamine is heated on a steam bath then 50 ml. of dry dioxane and 50 ml. of acetonitrile are added. To this mixture is added 4.2 g. (0.015 mole) of 3-benzoyl-2-methylpropionic acid, N-hydroxysuccinnimide ester, then the mixture is refluxed for 48 hours. The mixture is evaporated in vacuo. The residue is stirred with ethyl acetate and filtered. The filtrate is concentrated in vacuo and the residue is dissolved in dichloromethane. The dichloromethane is washed with sodium bisulfate and then extracted with saturated sodium bicarbonate solution. The sodium bicarbonate wash is added to dilute aqueous hydrochloric acid and the mixture is extracted with dichloromethane. The organic layer is dried over sodium sulfate and concentrated to an oil. The oil is crystallized from acetone-hexane to give [4R-(4R*,2'R*)]-3-(3-benzoyl-2-methylpropionyl)-4-thiazolidinecarboxylic acid as white crystals, m.p. 182°-183° C.; [α]D 23 -63°±4 (C, 0.24, CH3OH).

Workup

  1. additionA mixture of 2.0 g
  2. additionTo this mixture is added 4.2 g
  3. customThe mixture is evaporated in vacuo
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated in vacuo
  6. dissolutionthe residue is dissolved in dichloromethane
  7. washThe dichloromethane is washed with sodium bisulfate
  8. extractionextracted with saturated sodium bicarbonate solution
  9. washThe sodium bicarbonate wash
  10. additionis added to dilute aqueous hydrochloric acid
  11. extractionthe mixture is extracted with dichloromethane
  12. dry with materialThe organic layer is dried over sodium sulfate
  13. concentrationconcentrated to an oil
  14. customThe oil is crystallized from acetone-hexane

Sources & evidence

ORD record
ord-4da08e3346e241c98fa0a90780c4d469
Source dataset
uspto-grants-1983_02
Patent number
US04374249

Reaction notes

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