Hydrochloric Acid → HCID 178501087, compound

HRID 2260564Notes

Reaction equation

HRID 2260564 reaction equation
CC(C)([O-])C.[K+].[C:7]([NH:10][CH:11]([CH:13]1[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:15][CH2:14]1)[CH3:12])(=[O:9])[CH3:8].Cl>CO>[C:7]([NH:10][CH:11]([C@H:13]1[CH2:14][CH2:15][C@H:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:17][CH2:18]1)[CH3:12])(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 53910814HCID 53910814, compound

Product 1

HCID 178501087HCID 178501087, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium tert-butoxide (37.7 g) was added to a solution (200 ml) of a cis- and trans- mixture of methyl (+)-4-(1-acetamidoethyl)cyclohexanecarboxylate (38.0 g) in methanol and the mixture was refluxed under heating for 60 hours. After completion of the reaction, the mixture was concentrated under reduced pressure and the residue obtained was poured into ice water, neutralized with conc. hydrochloric acid and extracted with chloroform. The extract was washed with water, dried and concentrated under reduced pressure to give 21 g of methyl (+)-trans-4-(1-acetamidoethyl)cyclohexanecarboxylate. [α]D =+41.6° (methanol, c=1)

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 60 hours
  3. customAfter completion of the reaction
  4. concentrationthe mixture was concentrated under reduced pressure
  5. customthe residue obtained
  6. extractionextracted with chloroform
  7. washThe extract was washed with water
  8. customdried
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4062f6ba94924f6eb5e07f24b07abb9a
Source dataset
uspto-grants-1995_12
Patent number
US05478838

Reaction notes

Loading…