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4-Phthalimidobutyric acid → 2-[4-Oxo-4-[(2S)-2-(1-pyrrolidinylcarbonyl)-1-pyrrolidinyl]butyl]-1H-isoindole-1,3(2H)-dione

HRID 635895
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HRID 635895 반응식
[C:1]1(=[O:17])[N:5]([CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O)[C:4](=[O:12])[C:3]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:2]12.Cl.[NH:19]1[CH2:30][CH2:29][CH2:28][C@H:20]1[C:21]([N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:22]>C(Cl)(Cl)Cl.C(Cl)(=O)C(C)(C)C.C(N(CC)CC)C>[C:4]1(=[O:12])[N:5]([CH2:6][CH2:7][CH2:8][C:9]([N:19]2[CH2:30][CH2:29][CH2:28][C@H:20]2[C:21]([N:23]2[CH2:24][CH2:25][CH2:26][CH2:27]2)=[O:22])=[O:11])[C:1](=[O:17])[C:2]2=[CH:16][CH:15]=[CH:14][CH:13]=[C:3]12
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참가 물질

6

반응물 2

HCID 184114-Phthalimidobutyric acidHCID 69432689(2S)-2-(pyrrolidine-1-carbonyl)pyrrolidine hydrochloride

생성물 1

HCID 206400312-[4-Oxo-4-[(2S)-2-(1-pyrrolidinylcarbonyl)-1-pyrrolidinyl]butyl]-1H-isoindole-1,3(2H)-dione수율 57.2%

시약·촉매·용매 3

HCID 6212Chloroform용매2회HCID 8471Triethylamine용매
2회
HCID 62493Pivaloyl chloride용매

실험 절차

To a solution prepared by dissolving 1,17 g (5,0 mM) 4-phtalimido-butyric acid and 0,56 g (5,5 mM) triethylamin in 20 ml chloroform 0,61 g (5,0 mm) pivaloylchlorid were dropped at −15° C. under stirring. The reaction mixture was stirred for 1 hour at the above temperature and then a solution prepared by dissolving 1,03 g (5,0 mM) L-prolyl-pyrrolidin-hydrochloric acid salt in a mixture of 5 ml chloroform and 1,5 ml (1,1 g, 11,0 mM) triethylamine were dropwise added to it. Reaction mixture was stirred at room temperature for 4 hours, then it was washed successively with water, 30% cc. citric acid solution, saturated aqueous sodium bicarbonate solution, water and with saturated sodium chloride solution. The organic phase was dried on calcinated magnesium sulfate and it was evaporated. Crystallisation of the residue from a mixture of 5 ml chloroform and 10 ml petrolether yielded 1,1 g (53%) N-(4-phtalimido-butanoyl)-L-prolyl-pyrrolidin which melted at 148-149° C. The compounds of the general formula I were synthetised by the method as explained above starting from the corresponding compounds having general Formulas (II) and (III).

후처리

  1. customTo a solution prepared
  2. additionwere dropped at −15° C.
  3. stirringThe reaction mixture was stirred for 1 hour at the above temperature
  4. customa solution prepared
  5. additionwere dropwise added to it
  6. customReaction mixture
  7. stirringwas stirred at room temperature for 4 hours
  8. washit was washed successively with water, 30%
  9. customThe organic phase was dried
  10. customwas evaporated
  11. customCrystallisation of the residue
  12. additionfrom a mixture of 5 ml chloroform and 10 ml

출처 및 근거

ORD 기록
ord-1d45ed633a69433f8399d29a81146aca
출처 데이터셋
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06191161B1

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