HCID 14076767, compound → (5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-2(3H)-one

HRID 2380117Notes

Reaction equation

HRID 2380117 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:9](O)[C:10]#[C:11][C:12]([O:14]CC)=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(OCC)(=O)C>[C:22]([O:21][C:19]([NH:18][C@H:8]([C@H:9]1[O:14][C:12](=[O:13])[CH2:11][CH2:10]1)[CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)=[O:20])([CH3:23])([CH3:24])[CH3:25]

Participants

3

Reactant 1

HCID 14076767HCID 14076767, compound

Product 1

HCID 10946873(5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-2(3H)-oneYield 35%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 9.25 g of the oily ethyl (4RS, 5S)-6-cyclohexyl-5-(t-butoxycarbonylamino)-4-hydroxy-2-hexynate (prepared as described in Preparation 4) in 100 ml of ethyl acetate was subjected to a catalytic hydrogenation reaction using a Paar's apparatus in the presence of 5 g of 5% w/w palladium-onbarium sulfate at about 4 atmospheres pressure for 4 hours. At the end of this time, the catalyst was removed by filtration, and the filtrate was condensed by evaporation under reduced pressure. The residue was then dissolved in 120 ml of toluene, 3 ml of acetic acid was added to the resulting solution, and the mixture was heated under reflux for 3 hours. The solvent was then removed by distillation under reduced pressure, and the residue was purified by medium pressure silica gel column chromatography (using a 2:1 by volume mixture of hexane and diethyl ether as eluent), to give 3.71 g [yield 35% from N-(t-butoxycarbonyl)-L-cyclohexylalaninol] of the title compound as the product of lesser polarity.

Workup

  1. customfor 4 hours
  2. customAt the end of this time, the catalyst was removed by filtration
  3. customcondensed
  4. customby evaporation under reduced pressure
  5. dissolutionThe residue was then dissolved in 120 ml of toluene
  6. addition3 ml of acetic acid was added to the resulting solution
  7. temperaturethe mixture was heated
  8. temperatureunder reflux for 3 hours
  9. customThe solvent was then removed by distillation under reduced pressure
  10. customthe residue was purified by medium pressure silica gel column chromatography (
  11. additionby volume mixture of hexane and diethyl ether as eluent),

Sources & evidence

ORD record
ord-36cd78bd26bf433f85e2e8b4414dccf8
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

Loading…