Phthalimide potassium salt → HCID 67767352, compound

HRID 361585Notes

Reaction equation

HRID 361585 reaction equation
Cl[CH2:2][C:3]([N:5]1[C@@H:11]2[CH2:12][CH2:13][CH2:14][C@@H:10]2[C:9](=[O:15])[N:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:25])=[CH:19][CH:18]=2)[C:7]2[CH:35]=[CH:36][CH:37]=[CH:38][C:6]1=2)=[O:4].[C:39]1(=[O:49])[NH:43][C:42](=[O:44])[C:41]2=[CH:45][CH:46]=[CH:47][CH:48]=[C:40]12.[K]>CN(C=O)C.C(OCC)(=O)C.O>[C:29]1([CH2:28][CH2:27][NH:26][C:24](=[O:25])[NH:23][C:20]2[CH:19]=[CH:18][C:17]([CH2:16][N:8]3[C:9](=[O:15])[C@H:10]4[CH2:14][CH2:13][CH2:12][C@H:11]4[N:5]([C:3](=[O:4])[CH2:2][N:43]4[C:42](=[O:44])[C:41]5=[CH:45][CH:46]=[CH:47][CH:48]=[C:40]5[C:39]4=[O:49])[C:6]4[CH:38]=[CH:37][CH:36]=[CH:35][C:7]3=4)=[CH:22][CH:21]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 67767844HCID 67767844, compound

Product 1

HCID 67767352HCID 67767352, compoundYield 23.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3aR*,10aS*)-4-(chloroacetyl)-9-[4-[3-(2-phenylethyl)ureido]benzyl]-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (53 mg, 0.1 mmol) in DMF (1 mL) was added potassium phthalimide (20 mg, 0.11 mmol) and the mixture was stirred at room temperature for 24 hours. This reaction mixture was diluted with ethyl acetate and water and the aqueous layer was extracted with ethyl acetate. The pooled organic layer was washed with water and saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was crystallized from ethanol-diethyl ether to provide 15 mg (yield 23%) of the title compound. m.p. 145°-147° C.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe pooled organic layer was washed with water and saturated aqueous NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-1e05125254a14f0ab44f9500b0d21d3a
Source dataset
uspto-grants-1999_02
Patent number
US05866567

Reaction notes

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