Sulfuric Acid → HCID 86584274, compound

HRID 585492Notes

Reaction equation

HRID 585492 reaction equation
S(=O)(=O)(O)O.[CH2:6]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([CH:22]([C:28]([OH:30])=[O:29])[CH2:23][S:24][C:25](=[O:27])[CH3:26])[CH2:18][CH2:17]1)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:31][C:32](=[CH2:34])[CH3:33]>ClCCl>[CH2:6]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([CH:22]([C:28]([O:30][C:32]([CH3:34])([CH3:33])[CH3:31])=[O:29])[CH2:23][S:24][C:25](=[O:27])[CH3:26])[CH2:18][CH2:17]1)=[O:15])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 86584273HCID 86584273, compound

Product 1

HCID 86584274HCID 86584274, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfuric acid (1.15 ml) was added slowly to a solution of 4-(2-acetylsulfanyl-1-carboxy-ethyl)-piperidine-1-carboxylic acid benzyl ester (20.32 g) in dichloromethane (60 ml). The mixture was cooled in an acetone/dry ice bath and cooled isobutylene (60 ml) added. The mixture was transferred to a Parr high pressure apparatus and left to stir overnight then washed with water (30 ml), saturated sodium bicarbonate solution (30 ml) and brine (30 ml). After drying (Na2SO4) and filtering the solvent was removed under reduced pressure and the residue purified by column chromatography (SiO2, 20% ethyl acetate in hexane) to give the title compound (11.22 g, 60%) as an orange oil.

Workup

  1. temperatureThe mixture was cooled in an acetone/dry ice bath
  2. additionadded
  3. waitleft
  4. washthen washed with water (30 ml), saturated sodium bicarbonate solution (30 ml) and brine (30 ml)
  5. dry with materialAfter drying (Na2SO4)
  6. filtrationfiltering the solvent
  7. customwas removed under reduced pressure
  8. customthe residue purified by column chromatography (SiO2, 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ad8537dfee24467380d32c77878439ab
Source dataset
uspto-grants-2005_08
Patent number
US06933306B2

Reaction notes

Loading…