Cyclohexanol → HCID 53848100, compound

HRID 1154439Notes

Reaction equation

HRID 1154439 reaction equation
[I: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>CCO.CCO.CCO.CCO.[Ti].[F-].[K+]>[I: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

5

Reactant 2

HCID 7966CyclohexanolHCID 54532449HCID 54532449, compound

Product 1

HCID 53848100HCID 53848100, compound

Reagents, catalysts & solvents 2

HCID 2724286Titanium(IV)ethoxideCatalystHCID 522689Potassium FluorideSolvent

Procedure

12 g (26.6 mmol) of tert.butyl (S)-12,12a-dihydro-8-iodo-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylate, 70 ml (660 mmol) of cyclohexanol and 2 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 120 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 crystallization from ethyl acetate and hexane there is obtained cyclohexyl (S)-12,12a-dihydro-8-iodo-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylate of melting point 124°-125°.

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 crystallization from ethyl acetate and hexane

Sources & evidence

ORD record
ord-fa13f76bf100471590a8c372df2d440f
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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