Hydrochloric Acid → N-benzoyl-S-farnesylcysteine

HRID 1590448Notes

Reaction equation

HRID 1590448 reaction equation
[CH2:1]([S:16][CH2:17][C@@H:18]([C:20]([OH:22])=[O:21])[NH2:19])[CH:2]=[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH3:9])[CH3:4].[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.[OH-].[Na+]>C(OCC)(=O)C.C(N(CC)CC)C.CO>[C:23]([NH:19][C@H:18]([C:20]([OH:22])=[O:21])[CH2:17][S:16][CH2:1][CH:2]=[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH3:9])[CH3:4])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 122323S-Farnesyl cysteine

Product 1

HCID 54367624N-benzoyl-S-farnesylcysteine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22036596Ethyl acetate triethylamineSolvent

Procedure

S-farnesylcysteine was dissolved in dry ethyl acetate/triethylamine in a dry flask under nitrogen. equivalents of benzoylchloride was added in the cold and the suspension was allowed to stir for an hour. The solution was neutralized with dilute HCl. After evaporation, the product was applied to a preparative thin layer chromatography plate and eluted with hexane/ethyl acetate. The pure product was removed from the plate and eluted with methanol. Yields were in the range of 50-75%. The product showed the anticipated nmr and infrared spectra. The parent acid was prepared from the ester by the addition of one equivalent of sodium hydroxide in methanol. The product showed the expected nmr and infrared spectra.

Workup

  1. customAfter evaporation
  2. washeluted with hexane/ethyl acetate
  3. customThe pure product was removed from the plate
  4. washeluted with methanol
  5. customYields

Sources & evidence

ORD record
ord-b38c7273375c4c63987f915272276356
Source dataset
uspto-grants-1993_04
Patent number
US05202456

Reaction notes

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