Cyclopropanemethanol → HCID 53817368, compound

HRID 1154445Notes

Reaction equation

HRID 1154445 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(C)(C)C)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.O[CH2:27][CH:28]1[CH2:30][CH2:29]1>CCO.CCO.CCO.CCO.[Ti].[F-].[K+]>[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][CH2:27][CH:28]3[CH2:30][CH2:29]3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 75644CyclopropanemethanolHCID 54445650HCID 54445650, compound

Product 1

HCID 53817368HCID 53817368, compound

Reagents, catalysts & solvents 2

HCID 2724286Titanium(IV)ethoxideCatalystHCID 522689Potassium FluorideSolvent

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 (300 mmol) of hydroxymethyl-cyclopropane and 1.8 g (8 mmol) of tetraethyl orthotitanate are stirred at 120° overnight, the solution is evaporated to dryness and the residue is taken up in chloroform. The solution obtained is stirred for 0.5 hour with 40 ml of a saturated potassium fluoride solution, the resulting emulsion is filtered through siliceous earth, the organic phase is separated, washed with water, dried over magnesium sulphate and evaporated. By recrystallization from ethanol there is obtained cyclopropylmethyl (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 212°-213°.

Workup

  1. customthe solution is evaporated to dryness
  2. customThe solution obtained
  3. filtrationthe resulting emulsion is filtered through siliceous earth
  4. customthe organic phase is separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customBy recrystallization from ethanol

Sources & evidence

ORD record
ord-dba9f3c0354843db848a5d3c3e116e22
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

Loading…