Ethyl Acetate → Dimethyl (2R)-2-{[(benzyloxy)carbonyl]amino}pentanedioate

HRID 7285

Reaktionsgleichung

Reaktionsgleichung von HRID 7285
S(Cl)(Cl)=O.[NH2:5][C@@H:6]([C:12]([OH:14])=[O:13])[CH2:7]CC(O)=O.[C:15](=O)([O-])O.[K+].Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22].[C:31]([O:34][CH2:35]C)(=[O:33])[CH3:32]>CO.O>[CH2:24]([O:23][C:21]([NH:5][C@H:6]([CH2:7][CH2:32][C:31]([O:34][CH3:35])=[O:33])[C:12]([O:14][CH3:15])=[O:13])=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

8

Edukt 5

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 23327D-Glutamic AcidHCID 24386Thionyl ChlorideHCID 516893Potassium Bicarbonate

Produkt 1

HCID 86606597Dimethyl (2R)-2-{[(benzyloxy)carbonyl]amino}pentanedioate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Thionyl chloride (30 ml) was added to a cooled solution of D-glutamic acid (33.2 g) in methanol (250 ml) and the mixture subsequently heated under reflux for 16 h. On cooling, the mixture was concentrated under reduced pressure and the residue azeotroped with toluene to give a white solid. This was stirred with ethyl acetate, water and potassium hydrogen carbonate at 0° C. while benzyl chloroformate (30 ml) was added. The mixture was warmed to room temperature and stirred for 5 h. The separated organic phase was washed with water, dried (over magnesium sulphate) and concentrated under reduced pressure to provide a yellow oil. This oil was purified using flash column chromatography (silica, eluting with cyclohexane:ethyl acetate 2:1) to give the title compound (22.45 g) as an oil.

Aufarbeitung

  1. temperaturethe mixture subsequently heated
  2. temperatureunder reflux for 16 h
  3. temperatureOn cooling
  4. concentrationthe mixture was concentrated under reduced pressure
  5. customthe residue azeotroped with toluene
  6. customto give a white solid
  7. additionwas added
  8. washThe separated organic phase was washed with water
  9. dry with materialdried (over magnesium sulphate)
  10. concentrationconcentrated under reduced pressure
  11. customto provide a yellow oil
  12. customThis oil was purified
  13. washflash column chromatography (silica, eluting with cyclohexane:ethyl acetate 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-0d66f2913bdf4cf684ad6583f5f27c4b
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084139B2

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