HCID 21201657, compound → HCID 21201659, compound

HRID 1979335Notes

Reaction equation

HRID 1979335 reaction equation
COCN1C2C=C(OC)C=CC=2N(C2C=CC=CC=2)CC(N)C1=O.[O:25]=[C:26]1[NH:32][C:31]2[CH:33]=[C:34]([O:37][CH3:38])[CH:35]=[CH:36][C:30]=2[N:29]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:28][CH:27]1[NH:45][C:46]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47]>Br.C(O)(=O)C>[O:25]=[C:26]1[NH:32][C:31]2[CH:33]=[C:34]([O:37][CH3:38])[CH:35]=[CH:36][C:30]=2[N:29]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:28][CH:27]1[NH:45][C:46]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47]

Participants

3

Reactant 1

HCID 21201657HCID 21201657, compound

Product 1

HCID 21201659HCID 21201659, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

Preparation of 2-oxo-3-benzyloxycarbonylamino-5-phenyl-8-methoxy-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine 1-Methoxymethyl-2-oxo-3-amino-5-phenyl-8-methoxy-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (200 mg) was dissolved in 25% hydrobromic acid-acetic acid solution (1 ml), the solution was stirred for 2 hours. The reaction mixture was concentrated under reduced pressure, diisopropyl ether was added, the solid so precipitated was collected by filtration. The solid was dissolved in water (3 ml), a solution of benzyl chloroformate (140 mg) in tetrahydrofuran (3 ml) and 1N aqueous sodium hydroxide (2.8 ml) were successively added, and the mixture was stirred for one hours. Water was added to the resultant mixture, extracted with methylene chloride. The organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), to thereby obtain 107 mg of the titled compound as colorless amorphous.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, diisopropyl ether
  2. additionwas added
  3. customthe solid so precipitated
  4. filtrationwas collected by filtration
  5. dissolutionThe solid was dissolved in water (3 ml)
  6. additiona solution of benzyl chloroformate (140 mg) in tetrahydrofuran (3 ml) and 1N aqueous sodium hydroxide (2.8 ml) were successively added
  7. stirringthe mixture was stirred for one hours
  8. additionWater was added to the resultant mixture
  9. extractionextracted with methylene chloride
  10. washThe organic layer was successively washed with water and saturated brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-086c6cd9eb74496b9bdc0770da2dbea1
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

Loading…