Hydrochloric Acid → HCID 10382223, 화합물

HRID 277698노트

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HRID 277698 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 10382223HCID 10382223, 화합물

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 702Ethanol용매

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온도
-10 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-530b0d2e979c45578f221fdea2522585
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06358952B1

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