HCID 22393042, compound → HCID 10785324, compound

HRID 411403Notes

Reaction equation

HRID 411403 reaction equation
C(OC([NH:11][CH:12]1[N:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]2[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=2[N:14]([CH2:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:13]1=[O:38])=O)C1C=CC=CC=1>C(Cl)Cl>[NH2:11][CH:12]1[N:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]2[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=2[N:14]([CH2:29][C:30](=[O:37])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:13]1=[O:38]

Participants

3

Reactant 1

HCID 22393042HCID 22393042, compound

Product 1

HCID 10785324HCID 10785324, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(Benzoxycarbonyl)amino-2,3-dihydro-1-(2-oxo-2-phenylethyl)-5-phenyl-1H-1,4-benzodiazepin-2-one (3.7 g, 7.36 mmol) in 100 mL of anhydrous methylene chloride was cooled to 0° C. under nitrogen. A stream of anhydrous HBr gas was then bubbled through this solution for 1 h. The bubbler was removed and the reaction was warmed to room temperature under nitrogen. After stirring 1 h the reaction was concentrated under vacuum and the residue was redissolved in 20 mL of methylene chloride. The crude HBr salt of the product was precipitated from solution using 300 mL of anhydrous ether and collected by filtration as a light yellow solid. After washing with ether, the solid was dissolved in methylene chloride and saturated sodium bicarbonate. The layers were separated and the organic layer was extracted with saturated sodium bicarbonate. The combined aqueous layers were then back extracted twice with methylene chloride. The combined organic layers were extracted once with water and dried over sodium sulfate. After concentration under vacuum, 2.27 g of the product was obtained as an orange foam which was carried on without further purification.

Workup

  1. customA stream of anhydrous HBr gas was then bubbled through this solution for 1 h
  2. customThe bubbler was removed
  3. concentrationwas concentrated under vacuum
  4. dissolutionthe residue was redissolved in 20 mL of methylene chloride
  5. customThe crude HBr salt of the product was precipitated from solution
  6. filtrationcollected by filtration as a light yellow solid
  7. washAfter washing with ether
  8. dissolutionthe solid was dissolved in methylene chloride
  9. customThe layers were separated
  10. extractionthe organic layer was extracted with saturated sodium bicarbonate
  11. extractionThe combined aqueous layers were then back extracted twice with methylene chloride
  12. extractionThe combined organic layers were extracted once with water
  13. dry with materialdried over sodium sulfate
  14. concentrationAfter concentration under vacuum

Sources & evidence

ORD record
ord-31755dc977d844aea708d29998095342
Source dataset
uspto-grants-2003_05
Patent number
US06559141B2

Reaction notes

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