Bromide ion → HCID 21842254, compound

HRID 1737383Notes

Reaction equation

HRID 1737383 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[N:15][C:16]([C:17]3[O:18][CH2:19][C@@H:20]([C:22]([O:24][CH3:25])=[O:23])[N:21]=3)=[C:4]2[CH2:3]1.[Br-].C1C(C(OOC(C)(C)C)=O)=CC=CC=1.O>C1C=CC=CC=1>[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[N:15][C:16]([C:17]3[O:18][CH:19]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[N:21]=3)=[C:4]2[CH2:3]1

Participants

6

Reactant 4

HCID 259Bromide ionHCID 962WaterHCID 11966tert-Butyl peroxybenzoateHCID 53888673HCID 53888673, compound

Product 1

HCID 21842254HCID 21842254, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4.34 g (0.0128 mol) of methyl (S)-2-(5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-3-yl)-4,5-dihydro-oxazole-4-carboxylate in 160 ml of hot benzene was treated with 2.02 g (0.0141 mol) of copperl bromide and 3.75 ml (0.020 mol) of tert-butyl perbenzoate according to the method described in Tetr. Letters 1994, 35, 2481. The mixture was boiled at reflux for 1 hr., cooled and treated with 100 ml of water. The mixture was filtered, extracted with benzene and chromatographed over silica gel with ethyl acetate as the eluent. There were obtained 1.36 g (32%) of methyl 2-(5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-3-yl)-oxazole-4-carboxylate as a white solid. An analytical sample was recrystallized from hot methanol and gave white crystals; m.p. 264-265°.

Workup

  1. temperatureat reflux for 1 hr
  2. temperature, cooled
  3. filtrationThe mixture was filtered
  4. extractionextracted with benzene
  5. customchromatographed over silica gel with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-17ebb02a47804785866378873d41cf2f
Source dataset
uspto-grants-1999_10
Patent number
US05962450

Reaction notes

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