Sulfuric Acid → HCID 86735129, compound

HRID 972705Notes

Reaction equation

HRID 972705 reaction equation
[CH3:1][C:2](=[CH2:4])[CH3:3].OS(O)(=O)=O.[CH2:10]([O:17][C:18]([CH:20]([CH2:24][CH2:25][NH2:26])[C:21]([OH:23])=[O:22])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[C:2]([O:23][C:21](=[O:22])[CH:20]([C:18]([O:17][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:19])[CH2:24][CH2:25][NH2:26])([CH3:3])([CH3:1])[CH3:4]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 21202579HCID 21202579, compound

Product 1

HCID 86735129HCID 86735129, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

600 ml of liquefied isobutylene and 6 ml of conc. H2SO4 were added to a solution of 172 g of benzyloxycarbonyl-4-aminobutyric acid in 600 ml of methylene chloride. The mixture was shaken for 3 days at room temperature in an autoclave, the isobutylene was distilled off, and the methylene chloride solution was washed twice with 10% sodium carbonate solution and once with water, dried over sodium sulfate and concentrated in vacuo. The residue was dissolved in ether and chromatographed over 620 g of basic Al2O3. Elution with ether followed.

Workup

  1. distillationthe isobutylene was distilled off
  2. washthe methylene chloride solution was washed twice with 10% sodium carbonate solution and once with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in ether
  6. customchromatographed over 620 g of basic Al2O3
  7. washElution with ether

Sources & evidence

ORD record
ord-7f033cd1a86042d2a201efcc4e28ef34
Source dataset
uspto-grants-1977_10
Patent number
US04053588

Reaction notes

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