Guaiacol → HCID 54565554, compound

HRID 1154484Notes

Reaction equation

HRID 1154484 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](N3C=CN=C3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:33]1([O:40][CH3:41])[C:34](=[CH:36][CH:37]=[CH:38][CH:39]=1)[OH:35].CN(C)C=O>O>[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:35][C:34]3[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=3[O:40][CH3:41])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 460GuaiacolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 54332091(S)-1-[(8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl)carbonyl]imidazole

Product 1

HCID 54565554HCID 54565554, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.0 g (8.2 mmol) of 1-[[(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl]carbonyl]imidazole, 1.59 g (11.4 mmol) of powdered potassium carbonate, 1.48 g (11.5 mmol) of guaiacol and 20 ml of dry dimethylformamide is stirred at room temperature for 23 hours, then poured into 60 ml of water and extracted three times with methylene chloride. The organic extracts are washed twice with saturated sodium chloride solution, dried over magnesium sulphate and evaporated. The crude product is chromatographed on silica gel while eluting with ethyl acetate. After recrystallization from ethyl acetate, there is obtained o-methoxyphenyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 205°-206°.

Workup

  1. extractionextracted three times with methylene chloride
  2. washThe organic extracts are washed twice with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe crude product is chromatographed on silica gel
  6. washwhile eluting with ethyl acetate
  7. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-2f424c666db34944ae04b639969c2a5b
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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