Hydrochloric Acid → HCID 178501085, compound

HRID 2260568Notes

Reaction equation

HRID 2260568 reaction equation
CC(C)([O-])C.[K+].[C:7]([NH:10][C:11]([CH:14]1[CH2:19][CH2:18][CH:17]([C:20]([O:22][CH3:23])=[O:21])[CH2:16][CH2:15]1)([CH3:13])[CH3:12])(=[O:9])[CH3:8].Cl>CO>[C:7]([NH:10][C:11]([C@H:14]1[CH2:15][CH2:16][C@H:17]([C:20]([O:22][CH3:23])=[O:21])[CH2:18][CH2:19]1)([CH3:13])[CH3:12])(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 18998535Methyl 4-(1-acetamido-1-methylethyl)cyclohexanecarboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 178501085HCID 178501085, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium tert-butoxide (30.0 g) was added to a solution (150 ml) of a cis- and trans- mixture of methyl 4-(1-acetamido-1-methylethyl)cyclohexanecarboxylate (30.8 g) in methanol and the mixture was refluxed under heating for 40 hours. After completion of the reaction, the residue obtained by concentration under reduced pressure 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. The resultant crystals were recrystallized from methanol to give 24.5 g of methyl trans-4-(1-acetamido-1-methylethyl)cyclohexanecarboxylate.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 40 hours
  3. customAfter completion of the reaction
  4. customthe residue obtained by concentration under reduced pressure
  5. extractionextracted with chloroform
  6. washThe extract was washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe resultant crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-ce740386962342fb85f58eba5d86a087
Source dataset
uspto-grants-1995_12
Patent number
US05478838

Reaction notes

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