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

HRID 1180976

반응식

HRID 1180976 반응식
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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e7ca4b7c6569410ea603230741976bd6
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282497B2

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