Hydrochloric Acid → HCID 19898544, compound

HRID 1196465Notes

Reaction equation

HRID 1196465 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH3:3].[CH2:6]([O:13][C:14]([NH:16][CH:17]([CH2:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[CH:18]([OH:25])[C:19]([F:24])([F:23])[C:20](O)=[O:21])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl>C(OCC)C>[CH2:6]([O:13][C:14]([NH:16][CH:17]([CH2:26][CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1)[CH:18]([OH:25])[C:19]([F:24])([F:23])[C:20](=[O:21])[CH2:1][CH2:2][CH3:3])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 54074968HCID 54074968, compoundHCID 178455851HCID 178455851, compound

Product 1

HCID 19898544HCID 19898544, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a rapidly stirred solution of n-propylmagnesium bromide (9 mmol) in anhydrous diethyl ether (20 mL) was added dropwise a solution of 0.641 g (2,25 mmol) of 4-benzyloxycarbonylamino-5-cyclohexyl-2,2-difluoro-3-hydroxy pentanoic acid in anhydrous diethyl ether (10 mL). The mixture was refluxed under nitrogen for two hours after the addition of the acid was completed. The crude mixture was then poured onto a mixture of ice and 0.2N HCl (50 mL). The layers were separated and the aqueous phase was extracted with diethyl ether (3×20 mL). The combined organic layers were washed with a saturated sodium bicarbonate solution and brine. The organic layer was dried over anhydrous magnesium sulphate. Filtration and removal of the solvent in vacuo left an oil. The residue was purified by chromatography (silica gel, ethyl acetate/cyclohexane 1:1) to yield the expected ketone.

Workup

  1. temperatureThe mixture was refluxed under nitrogen for two hours
  2. additionafter the addition of the acid
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with diethyl ether (3×20 mL)
  5. washThe combined organic layers were washed with a saturated sodium bicarbonate solution and brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulphate
  7. filtrationFiltration and removal of the solvent in vacuo
  8. waitleft an oil
  9. customThe residue was purified by chromatography (silica gel, ethyl acetate/cyclohexane 1:1)

Sources & evidence

ORD record
ord-228ac66dafba4d64ac342babb2eaf9ae
Source dataset
uspto-grants-1992_05
Patent number
US05114927

Reaction notes

Loading…