Hydrogen Bromide → (3RS)-Amino-1-(tert-butylcarbonylmethyl)-2,3-dihydro-5-(2-pyridyl)-1H-1,4-benzodiazepin-2-one

HRID 2331Notes

Reaction equation

HRID 2331 reaction equation
C(OC([NH:6][CH:7]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[C:11]2[CH:20]=[CH:21][CH:22]=[CH:23][C:10]=2[N:9]([CH2:24][C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])=[O:26])[C:8]1=[O:31])=O)C.Br>C(Cl)Cl>[NH2:6][CH:7]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[C:11]2[CH:20]=[CH:21][CH:22]=[CH:23][C:10]=2[N:9]([CH2:24][C:25]([C:27]([CH3:29])([CH3:28])[CH3:30])=[O:26])[C:8]1=[O:31]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 10740914(3RS)-Ethyloxycarbonylamino-1-(tert-butylcarbonylmethyl)-2,3-dihydro-5-(2-pyridyl)-1H-1,4-benzodiazepin-2-one

Product 1

HCID 10498048(3RS)-Amino-1-(tert-butylcarbonylmethyl)-2,3-dihydro-5-(2-pyridyl)-1H-1,4-benzodiazepin-2-oneYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3RS)-Ethyloxycarbonylamino-1-(tert-butylcarbonylmethyl)-2,3-dihydro-5-(2-pyridyl)-1H-1,4-benzodiazepin-2-one (IV, 250 mg, 0.592 mmol) was taken up in dry DCM (10 ml) at 0° C. and saturated with dry HBr gas. The mixture was stoppered and stirred at r.t. for 64 h. The solvent was evaporated and the product partitioned between 1M HCl and EtOAc. The acid portion was basified and extracted with CHCl3 (×3). The extracts were combined and washed with brine, dried and evaporated to give a brown foam (188 mg, 91%), which was not purified further.

Workup

  1. customThe solvent was evaporated
  2. customthe product partitioned between 1M HCl and EtOAc
  3. extractionextracted with CHCl3 (×3)
  4. washwashed with brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-39eb4353217146abafbc990f86f0185c
Source dataset
uspto-grants-1998_03
Patent number
US05728829

Reaction notes

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