Hydrochloric Acid → HCID 23152375, compound

HRID 1012269Notes

Reaction equation

HRID 1012269 reaction equation
[CH2:1]([O:8][C:9]1[CH:38]=[CH:37][C:12]2[C:13]3[N:17]([CH2:18][CH2:19][C:20](=[O:21])[C:11]=2[CH:10]=1)[C:16]1[N:22]=[C:23]([C:26]([O:28]CC)=[O:27])[CH:24]=[CH:25][C:15]=1[C:14]=3[CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCCC1.CO>[CH2:1]([O:8][C:9]1[CH:38]=[CH:37][C:12]2[C:13]3[N:17]([CH2:18][CH2:19][C:20](=[O:21])[C:11]=2[CH:10]=1)[C:16]1[N:22]=[C:23]([C:26]([OH:28])=[O:27])[CH:24]=[CH:25][C:15]=1[C:14]=3[CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23152883HCID 23152883, compound

Product 1

HCID 23152375HCID 23152375, compoundYield 43.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 3-benzyloxy-12-cyclohexyl-6,7-dihydro-5-oxo-7a,8-diazadibenzo[a,e]azulene-9-carboxylate (50 mg, 0.10 mmol) in tetrahydrofuran (2 ml) and methanol (2 ml) was added 4N aqueous sodium hydroxide solution (1 ml), and the mixture was stirred with heating at 60° C. for 1 hr. The reaction mixture was allowed to cool to room temperature. 2N Hydrochloric acid (2 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. Hexane was added to the residue, and the precipitated solid was collected by filtration and dried in vacuo to give 3-benzyloxy-12-cyclohexyl-6,7-dihydro-5-oxo-7a,8-diazadibenzo[a,e]azulene-9-carboxylic acid (21 mg, yield 41%).

Workup

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. additionHexane was added to the residue
  8. filtrationthe precipitated solid was collected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-2df770fd356b45d080a292f418b1ac89
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

Loading…