Hydrochloric Acid → HCID 53799209, compound

HRID 1154444Notes

Reaction equation

HRID 1154444 reaction equation
[Br:1][C:2]1[C:7]2[C:8](=[O:25])[N:9]3[CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][C:19]([CH3:22])(C)[CH3:20])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:26]1(O)[CH2:31]CCC[CH2:27]1.Cl>CCO.CCO.CCO.CCO.[Ti].O>[Br:1][C:2]1[C:7]2[C:8](=[O:25])[N:9]3[CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][CH:19]3[CH2:20][CH2:31][CH2:26][CH2:27][CH2:22]3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7966CyclohexanolHCID 54445650HCID 54445650, compound

Product 1

HCID 53799209HCID 53799209, compound

Reagents, catalysts & solvents 2

HCID 2724286Titanium(IV)ethoxideCatalystHCID 962WaterSolvent

Procedure

8 g (20 mmol) of tert.butyl (S)-8-bromo-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylate, 25 g (250 mmol) of cyclohexanol and 1.8 g (8 mmol) of tetraethyl orthotitanate are stirred at 120° overnight, the excess cyclohexanol is removed in a water-jet vacuum and the residue is taken up in chloroform. The solution obtained is stirred for 0.5 hour with 40 ml of a 1:1 mixture of concentrated hydrochloric acid and water, the organic phase is separated, washed once with 1N hydrochloric acid and once with saturated sodium bicarbonate solution, dried over magnesium sulphate and evaporated. By recrystallization from ethanol there is obtained cyclohexyl (S)-8-bromo-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylate of melting point 203°-204°.

Workup

  1. customthe excess cyclohexanol is removed in a water-jet vacuum
  2. customThe solution obtained
  3. customthe organic phase is separated
  4. washwashed once with 1N hydrochloric acid and once with saturated sodium bicarbonate solution
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customBy recrystallization from ethanol

Sources & evidence

ORD record
ord-d4fb474457554f4ebe529d80670381e9
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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