Trifluoroacetic acid → 1-((7,7-Dimethyl-2-oxo-bicyclo(2.2.1)heptan-1-yl)methanesulfonyl)-4-(2-methylphenyl)-3-piperazinone

HRID 2293576노트

반응식

HRID 2293576 반응식
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[C:10](=[O:21])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.[CH3:29][C:30]1([CH3:43])[C:34]2([CH2:38][S:39](Cl)(=[O:41])=[O:40])[C:35]([CH2:37][CH:31]1[CH2:32][CH2:33]2)=[O:36].C(N(CC)CC)C>ClCCl.C(Cl)(Cl)Cl>[CH3:29][C:30]1([CH3:43])[CH:31]2[CH2:32][CH2:33][C:34]1([CH2:38][S:39]([N:8]1[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH3:20])[C:10](=[O:21])[CH2:9]1)(=[O:41])=[O:40])[C:35](=[O:36])[CH2:37]2

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 26579910-Camphorsulfonyl chlorideHCID 214763281,1-Dimethylethyl 4-(2-methylphenyl)-3-oxo-1-piperazinecarboxylate

생성물 1

HCID 214763111-((7,7-Dimethyl-2-oxo-bicyclo(2.2.1)heptan-1-yl)methanesulfonyl)-4-(2-methylphenyl)-3-piperazinone

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 1-t-butyloxycarbonyl-4-(2-methylphenyl)-3-piperazinone (0.25 g; 0.86 mmol) in dichloromethane (3 mL) was added TFA (1 mL). After 1 hour the solvents were removed under reduced pressure and the residue was taken up into chloroform and evaporated several times to remove excess TFA. The residue was dissolved in chloroform (5 mL) and added to the stirred solution was 10-camphorsulfonyl chloride (376 mg; 1.50 mmol) and triethylamine (0.38 mL; 2.7 mmol). After 12 hours, the mixture was diluted with chloroform (25 mL) and extracted with 5% aqueous HCl (25 mL), water (25 mL), and aqueous NaHCO3 (25 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 2:1 hexane-ethyl acetate as eluant. The title compound was obtained as a white foam from ether-hexane.

후처리

  1. customAfter 1 hour the solvents were removed under reduced pressure
  2. customevaporated several times
  3. customto remove excess TFA
  4. dissolutionThe residue was dissolved in chloroform (5 mL)
  5. additionadded to the stirred solution
  6. extractionextracted with 5% aqueous HCl (25 mL), water (25 mL), and aqueous NaHCO3 (25 mL)
  7. dry with materialThe organic phase was dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure
  10. customThe residue was purified by pressurized silica gel column chromatography

출처 및 근거

ORD 기록
ord-9312d2e50ec7416ba9e0fcc776846f2d
출처 데이터셋
uspto-grants-1997_11
특허 번호
US05686454

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