Dicyclohexylcarbodiimide → HCID 20344450, compound

HRID 372381Notes

Reaction equation

HRID 372381 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([S:19][CH2:20][CH:21]([CH2:25][C:26](=O)[NH2:27])[C:22]([OH:24])=[O:23])(=[O:18])[CH3:17]>N1C=CC=CC=1>[C:16]([S:19][CH2:20][CH:21]([CH2:25][C:26]#[N:27])[C:22]([OH:24])=[O:23])(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 203444533-Acetylthio-2-carbamoylmethylpropanoic acid

Product 1

HCID 20344450HCID 20344450, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Dicyclohexylcarbodiimide (1.03 g.) is added to a solution of 3-acetylthio-2-carbamoylmethylpropanoic acid (1.02 g.) in pyridine (18 ml.). After 5 hours stirring at room temperature, the precipitate is filtered off and the filtrate is concentrated to dryness, the residue is dissolved in ethyl acetate and extracted with saturated aqueous bicarbonate. The aqueous phase is acidified and extracted with ethyl acetate. This organic layer is dried and concentrated to dryness. The residue, 3-acetylthio-2-cyanomethylpropanoic acid is crystallized from ether-hexane, m.p. 110°-112°.

Workup

  1. filtrationthe precipitate is filtered off
  2. concentrationthe filtrate is concentrated to dryness
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. extractionextracted with saturated aqueous bicarbonate
  5. extractionextracted with ethyl acetate
  6. customThis organic layer is dried
  7. concentrationconcentrated to dryness
  8. customThe residue, 3-acetylthio-2-cyanomethylpropanoic acid is crystallized from ether-hexane, m.p. 110°-112°

Sources & evidence

ORD record
ord-83eb5f78a5a845ebb43a934c66ccec28
Source dataset
uspto-grants-1978_05
Patent number
US04091024

Reaction notes

Loading…