Dicyclohexylcarbodiimide → HCID 20344450, compound

HRID 65788Notes

Reaction equation

HRID 65788 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 five 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-9d17f63f07d94a6287cb95ae5e3b9173
Source dataset
uspto-grants-1978_12
Patent number
US04128721

Reaction notes

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