Hydrogen Bromide → HCID 18957791, compound

HRID 2379362Notes

Reaction equation

HRID 2379362 reaction equation
[CH:1]1([C:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]([CH2:17][CH2:18][CH3:19])[C:9](=[O:20])[CH:8]([NH:21]C(OCC3C=CC=CC=3)=O)[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br.CCOCC>C(O)(=O)C>[NH2:21][CH:8]1[N:7]=[C:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:17][CH2:18][CH3:19])[C:9]1=[O:20]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 18957769HCID 18957769, compound

Product 1

HCID 18957791HCID 18957791, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 5-cyclopentyl-1,3-dihydro-1-propyl-3(R,S)-[(benzyloxycarbonyl)amino]-2H-1,4-benzodiazepin-2-one (507 mg, 1.21 mmol) was added 45% hydrobromic acid in acetic acid (1 ml) and the mixture stirred at room temperature for 2 h. Anhydrous ether (10 ml) was then added and the mixture was stirred for 1.5 h before removing the solvent by pipette. The resulting solid was washed with more ether, filtered off and washed again with ether, before partitioning between dichloromethane (30 ml) and 2N sodium hydroxide solution (30 ml). The aqueous layer was re-extracted with more dichloromethane (2×30 ml), the organic extracts combined, dried (Na2SO4) and evaporated to leave the title compound (333 mg, 96%) as a colourless oil. 1H NMR (360 MHz, CDCl3) δ 0.81 (3H, t, J=7.4 Hz), 1.25-1.94 (9H, m); 2.16 (1H, m), 3.29 (1H, m), 3.56 (1H, m), 4.28 (1H, s), 4.30 (1H, m), 7.24 (1H, t, J=7.3 Hz), 7.31 (1H, d, J=7.9 Hz), 7.46 (1H, t of d, J=7.8 and 1.5 Hz), 7.53 (1H, dd, J=7.8 and 1.4 Hz).

Workup

  1. stirringthe mixture was stirred for 1.5 h
  2. custombefore removing the solvent by pipette
  3. washThe resulting solid was washed with more ether
  4. filtrationfiltered off
  5. washwashed again with ether
  6. custombefore partitioning between dichloromethane (30 ml) and 2N sodium hydroxide solution (30 ml)
  7. extractionThe aqueous layer was re-extracted with more dichloromethane (2×30 ml)
  8. dry with materialdried (Na2SO4)
  9. customevaporated

Sources & evidence

ORD record
ord-9cb0d1db6ab045e1839564afdde7d219
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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