Dicyclohexylamine → HCID 13104429, compound

HRID 1758696Notes

Reaction equation

HRID 1758696 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 warmed on a steam bath. To the mixture is added 50 ml. of dioxane, 50 ml. of acetonitrile and 4.2 g. (0.015 mole) of 3-benzoyl-2-methylpropionic acid, N-hydroxysuccinimide ester (prepared from 3-benzoyl-2-methylpropionic acid N-hydroxysuccinimide and N,N-dicyclohexylcarbodiimide in tetrahydrofuran). The mixture is refluxed for 48 hours and concentrated in vacuo. The residue is dissolved in dichloromethane, washed with sodium bisulfate and extracted with saturated sodium bicarbonate. The basic extract is added to dilute hydrochloric acid and 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 off-white crystals, m.p. 182°-183° C.; [α]D23 -63°±4 (c, 0.24, CH3OH).

Workup

  1. additionA mixture of 2.0 g
  2. additionTo the mixture is added 50 ml
  3. temperatureThe mixture is refluxed for 48 hours
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue is dissolved in dichloromethane
  6. washwashed with sodium bisulfate
  7. extractionextracted with saturated sodium bicarbonate
  8. extractionThe basic extract
  9. additionis added to dilute hydrochloric acid
  10. extractionextracted with dichloromethane
  11. dry with materialThe organic layer is dried over sodium sulfate
  12. concentrationconcentrated to an oil
  13. customThe oil is crystallized from acetone-hexane

Sources & evidence

ORD record
ord-d7bbdea371d0427997d92d63084579f6
Source dataset
uspto-grants-1983_02
Patent number
US04374249

Reaction notes

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