Hydrochloric Acid → HCID 67150454, compound

HRID 735750Notes

Reaction equation

HRID 735750 reaction equation
[C:1]([NH:9][C@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[C:16]([OH:18])=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:20]N(C)CCCN=C=NCC.C[O-].[Na+].Cl>CO.O1CCCC1.C(#N)C>[C:1]([NH:9][C@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[C:16]([O:18][CH3:20])=[O:17])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 126822626693-55-0HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 67150454HCID 67150454, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (1R,2S)-2-(benzoylamino)cyclohexanecarboxylic acid (2.47 g, 10 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (2.30 g, 12 mmol), acetonitrile (25 ml) and tetrahydrofuran (25 ml) was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, methanol (25 ml) was added, and the mixture was stirred at 60° C. for 3 hrs. The reaction mixture was concentrated under reduced pressure, dil. hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The extract was washed with aqueous sodium hydrogen carbonate solution, then with saturated brine and dried (over anhydrous MgSO4). The solvent was evaporated under reduced pressure. 28% Sodium methoxide in methanol solution (1.93 g, 10 mmol) and methanol (30 ml) were added to the residue and the mixture was heated under reflux for 5 hrs. 1N Hydrochloric acid (11 ml) was added under ice-cooling, and methanol was evaporated under reduced pressure. Aqueous sodium hydrogen carbonate solution was added to the obtained residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried (over anhydrous MgSO4), and the solvent was evaporated under reduced pressure. The obtained solid was collected by filtration and washed with diisopropy ether to give methyl (1S,2S)-2-(benzoylamino)cyclohexanecarboxylate (1.33 g, 51%) as a colorless powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, methanol (25 ml)
  2. additionwas added
  3. stirringthe mixture was stirred at 60° C. for 3 hrs
  4. concentrationThe reaction mixture was concentrated under reduced pressure, dil. hydrochloric acid
  5. additionwas added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with aqueous sodium hydrogen carbonate solution
  8. dry with materialwith saturated brine and dried (over anhydrous MgSO4)
  9. customThe solvent was evaporated under reduced pressure
  10. temperaturethe mixture was heated
  11. temperatureunder reflux for 5 hrs
  12. temperaturecooling
  13. custommethanol was evaporated under reduced pressure
  14. additionAqueous sodium hydrogen carbonate solution was added to the obtained residue
  15. extractionthe mixture was extracted with ethyl acetate
  16. washThe extract was washed with saturated brine
  17. dry with materialdried (over anhydrous MgSO4)
  18. customthe solvent was evaporated under reduced pressure
  19. filtrationThe obtained solid was collected by filtration
  20. washwashed with diisopropy ether

Sources & evidence

ORD record
ord-a9ab033c8f434ef89bcbb47759f5af6c
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

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