Hydrogen chloride-ethyl acetate → HCID 22405244, compound

HRID 441259Notes

Reaction equation

HRID 441259 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([CH2:16][N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]([C:28](=[O:51])[C:29]3[CH:34]=[CH:33][C:32]([NH:35][C:36](=[O:50])[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[C:43]4[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=4)=[CH:31][CH:30]=3)[CH2:20][CH2:19][C:18]2=[O:52])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C(OCC)(=O)C.Cl>C(OCC)(=O)C>[CH3:49][C:46]1[CH:47]=[CH:48][C:43]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[C:36]([NH:35][C:32]2[CH:33]=[CH:34][C:29]([C:28]([N:21]3[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[N:17]([CH2:16][C:14]([N:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)=[O:15])[C:18](=[O:52])[CH2:19][CH2:20]3)=[O:51])=[CH:30][CH:31]=2)=[O:50])=[CH:44][CH:45]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 22405115HCID 22405115, compound

Product 1

HCID 22405244HCID 22405244, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-[(4-tert-butoxycarbonyl-1piperazinyl)carbonylmethyl]-5-{4-[2-(4-methylphenyl)benzoylamino]benzoyl}-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (150 mg) in ethyl acetate (5 ml) was added 4N hydrogen chloride - ethyl acetate solution, and then the mixture was stirred at ambient temperature for 12 hours. The solvents were evaporated in vacuo and the residue was diluted with saturated aqueous sodium bicarbonate solution, and then the aqueous layer was extracted with ethyl acetate. Drying, filtering and the removal of solvents afforded a crude product. The crude product was chromatographed on silica gel (20% methanol in chloroform) to give 5-{4-[2-(4-methylphenyl)benzoylamino]benzoyl}-1-[(1-piperazinyl)carbonylmethyl]-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (58 mg) as a white powder.

Workup

  1. customThe solvents were evaporated in vacuo
  2. additionthe residue was diluted with saturated aqueous sodium bicarbonate solution
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. customDrying
  5. filtrationfiltering
  6. customthe removal of solvents
  7. customafforded a crude product
  8. customThe crude product was chromatographed on silica gel (20% methanol in chloroform)

Sources & evidence

ORD record
ord-becbb5b441e34e75a94da15f17f80055
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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