2H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo- → HCID 67767530, compound

HRID 361575Notes

Reaction equation

HRID 361575 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:13]=[C:14]([CH:31]=[CH:32][CH:33]=1)[CH2:15][N:16]1[C:22](=[O:23])[C@H:21]2[CH2:24][CH2:25][CH2:26][C@H:20]2[NH:19][C:18]2[CH:27]=[CH:28][CH:29]=[CH:30][C:17]1=2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:34]1(=[O:48])[N:38]([CH2:39][C:40](Cl)=[O:41])[C:37](=[O:43])[C:36]2=[CH:44][CH:45]=[CH:46][CH:47]=[C:35]12.C([O-])(O)=O.[Na+]>ClCCCl.O>[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:13]=[C:14]([CH:31]=[CH:32][CH:33]=1)[CH2:15][N:16]1[C:22](=[O:23])[C@H:21]2[CH2:24][CH2:25][CH2:26][C@H:20]2[N:19]([C:40](=[O:41])[CH2:39][N:38]2[C:37](=[O:43])[C:36]3=[CH:44][CH:45]=[CH:46][CH:47]=[C:35]3[C:34]2=[O:48])[C:18]2[CH:27]=[CH:28][CH:29]=[CH:30][C:17]1=2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-HCID 516892Sodium BicarbonateHCID 67767816HCID 67767816, compound

Product 1

HCID 67767530HCID 67767530, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a solution of (3aR*,10aS*)-9-[3-(benzyloxycarbonylamino)benzyl]-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (1.9 g, 4.3 mmol) in 1,2-dichloroethane (50 mL) was added phthalimidoacetyl chloride (1.1 g, 4.7 mmol) at room temperature and the mixture was refluxed for 17 hours. After cooling, saturated aqueous NaHCO3 solution (30 mL) was added and the mixture was diluted with water and extracted with 2 portions of chloroform. The pooled organic layer was washed with saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was crystallized from diethyl ether to provide 1.5 g (yield 55%) of the title compound. m.p. 224°-225° C.

Workup

  1. temperaturethe mixture was refluxed for 17 hours
  2. temperatureAfter cooling
  3. extractionextracted with 2 portions of chloroform
  4. washThe pooled organic layer was washed with saturated aqueous NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-c16cf7ef2b8046cb892b543097a87f42
Source dataset
uspto-grants-1999_02
Patent number
US05866567

Reaction notes

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