Cyclohexanol → HCID 22828757, compound

HRID 1154494Notes

Reaction equation

HRID 1154494 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:26])[N:9]3[CH2:25][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][C:3]=1[F:27].[CH:28]1(O)[CH2:33]CCC[CH2:29]1>CCO.CCO.CCO.CCO.[Ti]>[Cl:1][C:2]1[C:7]2[C:8](=[O:26])[N:9]3[CH2:25][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[CH2:22][CH2:33][CH2:28][CH2:29][CH2:20]3)=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[F:27]

Participants

4

Reactant 2

HCID 7966CyclohexanolHCID 70040464HCID 70040464, compound

Product 1

HCID 22828757HCID 22828757, compound

Reagents, catalysts & solvents 1

HCID 2724286Titanium(IV)ethoxideCatalyst

Procedure

A mixture of 4.0 g (10 mmol) of tert.butyl (S)-8-chloro-7-fluoro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate, 0.8 g (3 mmol) of tetraethyl orthotitanate and 15 ml of cyclohexanol is stirred at 120° overnight, evaporated to dryness, the residue is taken up in methylene chloride, the solution obtained is washed successively with 40 ml of 5N hydrochloric acid, water and saturated sodium bicarbonate solution, dried over magnesium sulphate and evaporated. There is obtained cyclohexyl (S)-8-chloro-7-fluoro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 163°-166°.

Workup

  1. customevaporated to dryness
  2. customthe solution obtained
  3. washis washed successively with 40 ml of 5N hydrochloric acid, water and saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-ff15d484f02c4dc48b9b7736522cc502
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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