Hydrochloric Acid → HCID 91356769, compound

HRID 406347Notes

Reaction equation

HRID 406347 reaction equation
[C:1]([O:5][C:6]([NH:8][NH:9][CH:10]1[CH2:15][CH2:14][C:13]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)([C:16](OC)=[O:17])[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C(OCC)C.Cl>CO>[C:1]([O:5][C:6](=[O:7])[NH:8][N:9]1[C:16](=[O:17])[C:13]2([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)[CH2:14][CH2:15][CH:10]1[CH2:11][CH2:12]2)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 666188011,1-Dimethylethyl 2-[4-(methoxycarbonyl)-4-[4-(trifluoromethyl)phenyl]cyclohexyl]hydrazinecarboxylate

Product 1

HCID 91356769HCID 91356769, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-(N′-tert-butoxycarbonylhydrazino)-1-(4-trifluoromethylphenyl)cyclohexanecarboxylate (74.5 mg) was dissolved in methanol (1.5 mL), followed by addition of a 1 N sodium hydroxide solution (1 mL) The mixture was stirred at room temperature for 15 hours and then stirred with heating under reflux for 11 hours and 30 minutes. After leaving to cool, diethyl ether was added to the reaction solution, followed by neutralization with 1 N hydrochloric acid. The organic layer was separated and then washed with brine. The resulting organic layer was dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (35.7 mg). The property values of the compound are as follows.

Workup

  1. stirringstirred
  2. temperaturewith heating
  3. temperatureunder reflux for 11 hours and 30 minutes
  4. customAfter leaving
  5. temperatureto cool
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  9. customThe drying agent was separated by filtration
  10. concentrationthe organic layer was concentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0b9000ffa5b54c4d9f17fb0a710744ad
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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