Cyclopropanemethanol → HCID 53675640, compound

HRID 1154436Notes

Reaction equation

HRID 1154436 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(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]>[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][CH2:27][CH:28]3[CH2:30][CH2:29]3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 75644CyclopropanemethanolHCID 54532449HCID 54532449, compound

Product 1

HCID 53675640HCID 53675640, compound

Reagents, catalysts & solvents 1

HCID 2724286Titanium(IV)ethoxideCatalyst

Procedure

3.0 g (5.5 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, 20 ml (250 mmol) of hydroxymethyl-cyclopropane and 0.7 g (3 mmol) of tetraethyl orthotitanate are stirred at 120° overnight, the solution is evaporated to dryness, the residue is taken up in chloroform and stirred for 0.5 hour with 30 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 ethyl acetate there is obtained cyclopropylmethyl (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 190°-191°.

Workup

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

Sources & evidence

ORD record
ord-a67b0268e2c84ace9e6d07f0b3d59f19
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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