Hydrogen Bromide → 3-Amino-1-isobutyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

HRID 459898Notes

Reaction equation

HRID 459898 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][CH:30]([CH3:32])[CH3:31])[C:13]1=[O:33])=O)C1C=CC=CC=1.Br>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][CH:30]([CH3:31])[CH3:32])[C:13]1=[O:33]

Participants

4

Reactant 2

HCID 260Hydrogen Bromide2×HCID 184442513-Benzyloxycarbonylamino-1-isobutyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

Product 1

HCID 197568673-Amino-1-isobutyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-benzyloxycarbonylamino-1-isobutyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (880 mg, 1.99 mmol) in methylene chloride (10 mL) was cooled to 0° C. and saturated with hydrogen bromide gas. The reaction was refluxed overnight, cooled, saturated with hydrogen bromide and refluxed 3 h. Solvent was evaporated and the reaction worked up with saturated sodium bicarbonate solution and methylene chloride. The title compound was isolated by column chromatography (silica gel, 0 to 10% methanol in methylene chloride gradient elution). Enantiomers were separated on a Chiralpak AS column (silica gel, 30% hexane, 70% ethanol with diethylamine, isocratic elution), yielding enantiomer A of the title compound (91.9 mg) and enantiomer B of the title compound (87.1 mg).

Workup

  1. temperatureThe reaction was refluxed overnight
  2. temperaturerefluxed 3 h
  3. customSolvent was evaporated

Sources & evidence

ORD record
ord-b0a664eb15f047c6a1eb53ceda65aaed
Source dataset
uspto-grants-2007_03
Patent number
US07196079B2

Reaction notes

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