Sulfuric Acid → HCID 86584274, compound

HRID 992420Notes

Reaction equation

HRID 992420 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-c51321d487bb442eacc0a50c8342c814
Source dataset
uspto-grants-2002_10
Patent number
US06469020B2

Reaction notes

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