Hydrochloric Acid → HCID 10382223、化合物

HRID 277698ノート

反応式

HRID 277698 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=O)[N:8]([C@@H:11]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6](=[O:7])[C:5]2=[CH:24][CH:25]=1.Cl>C(O)C.[Zn]>[NH2:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:24][CH:25]=1)[C:6](=[O:7])[N:8]([C@@H:11]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:9]2

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 10043327diethyl(S)-2-(4-aminophthalimido)glutarate

生成物 1

HCID 10382223HCID 10382223、化合物

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 702Ethanol溶媒

反応条件

温度
-10 °C

実験手順

A solution of diethyl (S)-2-(4-aminophthalimido)glutarate (10.5 g, 30.2 mmol) in ethanol (150 ml) was cooled in an acetonitrile/CO2 bath. Concentrated HCl (25 ml) was added followed by 30 mesh granular Zn (10.5 g, 0.161 mole) (Fisher) when the internal temperature has reached −40° C. The reaction mixure was stirred 1.5 hours at this temperature and a further 1 hour at −10° C. The excess of Zn was filtered from the solution, 10% palladium on carbon (1.0 g) was added, and the solution shaken under hydrogen at (30-50 psi) overnight. The catalyst was removed by filtration through celite and the filtrate concentrated in vacuo. The residue was absorbed onto silica gel (15 g) and purified by chromatography on silica gel (440 g) eluting with ethyl acetate:methylene chloride (1:14 g).

後処理

  1. customhas reached −40° C
  2. filtrationThe excess of Zn was filtered from the solution, 10% palladium on carbon (1.0 g)
  3. additionwas added
  4. stirringthe solution shaken under hydrogen at (30-50 psi) overnight
  5. customThe catalyst was removed by filtration through celite
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe residue was absorbed onto silica gel (15 g)
  8. custompurified by chromatography on silica gel (440 g)
  9. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-530b0d2e979c45578f221fdea2522585
出典データセット
uspto-grants-2002_03
特許番号
US06358952B1

反応ノート

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