Bromide ion → HCID 21842247, compound

HRID 1737388Notes

Reaction equation

HRID 1737388 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:26])[N:9]([CH3:25])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:17][CH2:18][C@@H:19]([C:21]([O:23][CH3:24])=[O:22])[N:20]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br-].C1C(C(OOC(C)(C)C)=O)=CC=CC=1.O>C1C=CC=CC=1>[Cl:1][C:2]1[C:7]2[C:8](=[O:26])[N:9]([CH3:25])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:17][CH:18]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[N:20]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 259Bromide ionHCID 962WaterHCID 11966tert-Butyl peroxybenzoateHCID 54469685HCID 54469685, compound

Product 1

HCID 21842247HCID 21842247, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 6.80 g (0.0181 mol) of methyl (S)-2-(7-chloro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-3-yl)-4,5-dihydro-oxazole-4-carboxylate in 700 ml of hot benzene was treated with 2.86 g (0.0199 mol) of copperl bromide and 5.1 ml (0.0272 mol) of tert-butyl perbenzoate according to the method described in Tetr. Letters 1994, 35, 2481. The mixture was boiled at reflux for 20 min., cooled and treated with 300 ml of water. The mixture was filtered, extracted with dichloromethane and chromatographed over silica gel with ethyl acetate as the eluent. There were obtained 3.15 g (47%) of methyl 2-(7-chloro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-3-yl)-oxazole-4-carboxylate as white crystals; m.p. 266-268°.

Workup

  1. temperatureat reflux for 20 min.
  2. temperaturecooled
  3. filtrationThe mixture was filtered
  4. extractionextracted with dichloromethane
  5. customchromatographed over silica gel with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-aae94e86963a40448c30eea70b149bdd
Source dataset
uspto-grants-1999_10
Patent number
US05962450

Reaction notes

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