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

HRID 7285

反応式

HRID 7285 の反応式
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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0d66f2913bdf4cf684ad6583f5f27c4b
出典データセット
uspto-grants-2006_08
特許番号
US07084139B2

関連ノート

読み込み中…