Acetic Acid → HCID 24990993, compound

HRID 425958Notes

Reaction equation

HRID 425958 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:15])[C@H:5]([OH:14])[C@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:7].Cl.C(N(CC)CC)C.C(O)(=O)C>CO.C(OCC)(=O)C>[C:4]([OH:15])(=[O:3])[CH3:5].[CH3:2][O:3][C:4](=[O:15])[C@H:5]([OH:14])[C@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:7]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 44475322HCID 44475322, compound

Product 1

HCID 24990993HCID 24990993, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2R,3S)-3-Phenylisoserine methyl ester hydrochloride (XI) (20.0 g, 0.092 mole) was suspended in methanol (140.0 g). 7.0 g gaseous HCl was slowly added keeping the temperature at about 25° C. After completion of the addition the mixture was heated at reflux for further 3 hours. After distilling off 85.0 g of methanol the mixture was cooled down to room temperature. After the addition of 220.0 g ethyl acetate 20.0 g of triethyl amine (0.2 mole) was added, keeping the temperature at 25° C. After distillation of 195.0 g of solvent further 195.0 g ethyl acetate were added. The suspension was filtered at 50° C. and the residue was washed with 50.0 g ethyl acetate. The filtrate was cooled to 40° C. and 9.0 g of acetic acid (0.15 mole) were added slowly until formation of a precipitate. The mixture was cooled down to 0° C. and stirred for further 2 hours. The product was filtered off, washed with 30.0 g ethyl acetate and vacuum dried at 50° C. Yield: 20.3 g (0.08 mole, 87%).

Workup

  1. customat about 25° C
  2. additionAfter completion of the addition the mixture
  3. temperaturewas heated
  4. temperatureat reflux for further 3 hours
  5. distillationAfter distilling off 85.0 g of methanol the mixture
  6. additionwas added
  7. customat 25° C
  8. distillationAfter distillation of 195.0 g of solvent further 195.0 g ethyl acetate
  9. additionwere added
  10. filtrationThe suspension was filtered at 50° C.
  11. washthe residue was washed with 50.0 g ethyl acetate
  12. temperatureThe filtrate was cooled to 40° C.
  13. temperatureThe mixture was cooled down to 0° C.
  14. filtrationThe product was filtered off
  15. washwashed with 30.0 g ethyl acetate and vacuum
  16. customdried at 50° C

Sources & evidence

ORD record
ord-171e3fb4b3cc4793a0d4fd2d1cf8032e
Source dataset
uspto-grants-2012_01
Patent number
US08106231B2

Reaction notes

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