Sulfuric Acid → HCID 19833139, compound

HRID 1639380Notes

Reaction equation

HRID 1639380 reaction equation
S(=O)(=O)(O)O.[C:6]([NH:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:16]=1[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[O:14])(=[O:8])[CH3:7].[CH3:27][C:28](=[CH2:30])[CH3:29]>O1CCCC1>[C:6]([NH:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:16]=1[CH2:17][CH2:18][C:19]([O:21][C:28]([CH3:30])([CH3:29])[CH3:27])=[O:20])=[O:14])(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 198331272-(4-Acetamidobutyryl)-5-chlorohydrocinnamic acid

Product 1

HCID 19833139HCID 19833139, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.3 ml of concentrated sulfuric acid is added to a solution of 10.00 g (0.032 mol) of 2-(4-acetamidobutyryl)-5-chlorohydrocinnamic acid in 40 ml of tetrahydrofuran in a steel autoclave and about 60 ml of isobutylene are condensed. The mixture is stirred at room temperature for 30 days. The solution is concentrated, extracted with methylene chloride/water, dried with magnesium sulfate and the solvent is distilled in a vacuum. Chromatography with ethyl acetate on aluminum oxide and then on silica gel gives t-butyl 2-(4-acetamidobutyryl)-5-chlorohydrocinnamate as a colorless oil.

Workup

  1. customcondensed
  2. concentrationThe solution is concentrated
  3. extractionextracted with methylene chloride/water
  4. dry with materialdried with magnesium sulfate
  5. distillationthe solvent is distilled in a vacuum

Sources & evidence

ORD record
ord-bdbe19ee074d492c975a53753f2b74fd
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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