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

HRID 2293576ノート

反応式

HRID 2293576 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9312d2e50ec7416ba9e0fcc776846f2d
出典データセット
uspto-grants-1997_11
特許番号
US05686454

反応ノート

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