Dichloromethane → HCID 21201536, compound

HRID 1979313Notes

Reaction equation

HRID 1979313 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([CH2:15][N:16]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:19][CH:18]([NH:33][C:34]([NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([NH:45][S:46]([CH3:49])(=[O:48])=[O:47])=[O:44])[CH:38]=2)=[O:35])[C:17]1=[O:50])=[O:14])(C)(C)C.C(Cl)Cl.C(=O)(O)[O-].[Na+]>ClCCCl>[CH3:49][S:46]([NH:45][C:43]([C:39]1[CH:38]=[C:37]([NH:36][C:34](=[O:35])[NH:33][CH:18]2[C:17](=[O:50])[N:16]([CH2:15][C:13]([OH:14])=[O:12])[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[N:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:19]2)[CH:42]=[CH:41][CH:40]=1)=[O:44])(=[O:47])=[O:48]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 21201549HCID 21201549, compound

Product 1

HCID 21201536HCID 21201536, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Trifluoroacetic acid (0.32 ml) was added to a solution of 1-(1-tert-butoxycarbonylmethyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-methylsulfonylaminocarbonylphenyl)urea (400 mg) obtained from example 16 in anhydrous 1,2-dichloroethane (10 ml), the mixture was refluxed for 5 hours. Methylene chloride (30 ml) and saturated aqueous sodium bicarbonate were added to the reaction mixture and separated into organic layer and aqueous layer, the aqueous layer was adjusted to pH 2 with 1N hydrochloric acid, and extracted with ethyl acetate. The extraction was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Isopropyl ether was added to the residue for trituration and filtrated, to thereby obtain 226 mg of the title compound as a yellow solid (Yield: 64.0%).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. customseparated into organic layer and aqueous layer
  3. extractionextracted with ethyl acetate
  4. extractionThe extraction
  5. washwas washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. additionIsopropyl ether was added to the residue for trituration
  9. filtrationfiltrated

Sources & evidence

ORD record
ord-b7789bd7c820468fb97510494c471910
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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