Chloroform → HCID 178453988, compound

HRID 1445353Notes

Reaction equation

HRID 1445353 reaction equation
C(Cl)(Cl)Cl.[C:5]([O:9][C:10]([NH:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([NH2:19])[CH2:15][CH2:14]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].[N+:20]([C:23]1[CH:33]=[CH:32][CH:31]=[C:25]2[C:26]([O:28][C:29](=O)[C:24]=12)=[O:27])([O-:22])=[O:21].C(N1C=CN=C1)(N1C=CN=C1)=O>O>[C:5]([O:9][C:10]([NH:12][C@H:13]1[CH2:14][CH2:15][C@H:16]([N:19]2[C:29](=[O:28])[C:24]3[C:25](=[CH:31][CH:32]=[CH:33][C:23]=3[N+:20]([O-:22])=[O:21])[C:26]2=[O:27])[CH2:17][CH2:18]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 216313-Nitrophthalic anhydrideHCID 682631,1'-CarbonyldiimidazoleHCID 178419079HCID 178419079, compound

Product 1

HCID 178453988HCID 178453988, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15 ml of a chloroform solution containing 500 mg of N-tert-butoxycarbonyl-trans-1,4-cyclohexanediamine and 540 mg of 3-nitrophthalic anhydride was refluxed for 1 hour. After cooling, 756 mg of carbonyldiimidazole was added to the mixture and the resulting mixture was stirred at room temperature for 15 hours. Water was added to the reaction mixture and the resulting mixture was extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel flash column chromatography to obtain 900 mg of N-tert-butoxycarbonyl-trans-4-(1,3-dioxo-4-nitro-2-isoindolinyl)-cyclohexylamine.

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureAfter cooling
  3. extractionthe resulting mixture was extracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-96f10bdad14442148260fc23a3468cee
Source dataset
uspto-grants-2010_02
Patent number
US07666869B2

Reaction notes

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