Hydrochloric Acid → HCID 70385785, compound

HRID 1607407Notes

Reaction equation

HRID 1607407 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]([C:17]#[N:18])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[CH3:2].[ClH:20]>C(O)C.[Pt]=O>[ClH:20].[CH2:1]([O:3][C:4](=[O:19])[CH:5]([CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[CH2:17][NH2:18])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12308369HCID 12308369, compound

Product 1

HCID 70385785HCID 70385785, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A solution of 6.22 g of 2-cyano-3-(1-naphthyl)propionic acid ethyl ester and 50 ml of a 2N-hydrochloric acid in 300 ml of ethanol was hydrogenated over 600 mg of platinum oxide under atmospheric pressure. After filtration of the catalyst, the filtrate was concentrated under reduced pressure, and water was added to the residue. The mixture was washed with diethyl ether to remove neutral materials. The aqueous layer was neutralized by adding sodium bicarbonate, and then extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. An absolute ethanol solution containing hydrogen chloride was added to the organic layer. The organic layer was concentrated under reduced pressure, and hexane was added to the residue, and the resulting precipitates were collected by filtration to obtain 3.20 g of 3-amino-2-(1-naphthylmethyl)propionic acid ethyl ester hydrochloride as colorless crystals.

Workup

  1. filtrationAfter filtration of the catalyst
  2. concentrationthe filtrate was concentrated under reduced pressure, and water
  3. additionwas added to the residue
  4. washThe mixture was washed with diethyl ether
  5. customto remove neutral materials
  6. additionby adding sodium bicarbonate
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. additionAn absolute ethanol solution containing hydrogen chloride
  11. additionwas added to the organic layer
  12. concentrationThe organic layer was concentrated under reduced pressure, and hexane
  13. additionwas added to the residue
  14. customthe resulting precipitates
  15. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-7b195e5aac624785b278db44880c8e92
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

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