Acetylcysteamine → HCID 86608484, compound

HRID 1594539Notes

Reaction equation

HRID 1594539 reaction equation
[CH2:1]([S:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:11])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH3:6].C(NCCS)(=O)C.C(NCCS)(=O)C>C(Cl)(Cl)Cl>[CH2:1]([S:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:11])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH3:6]

Participants

4

Reactant 2

HCID 14484AcetylcysteamineHCID 86608485HCID 86608485, compound

Product 1

HCID 86608484HCID 86608484, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Octadecyl S-sorbyl-3-mercaptopropionate-N-acetylcysteamine monoadducts (3 and 4). In a 50-mL round-bottom flask, 181 mg (0.40 mmol) of OSM was dissolved in 10 mL of chloroform, which was purged with nitrogen for 15 minutes prior to use. 30 μL (0.28 mmol) of N-acetylcysteamine and 39 μL (0.28 mmol) of triethylanine were added, and the solution was stirred under reflux in a nitrogen atmosphere for 2 hours. The solvent was evaporated and the mixture of monoadducts was isolated by preparative TLC with 3% methanol in chloroform. Rf=0.66. The isolated monoadducts mixture was spotted onto another preparative TLC plate, and the monoadducts were separated by repetitive developments with 3% methanol in chloroform.

Workup

  1. customwhich was purged with nitrogen for 15 minutes
  2. temperatureunder reflux in a nitrogen atmosphere for 2 hours
  3. customThe solvent was evaporated
  4. additionthe mixture of monoadducts
  5. customwas isolated by preparative TLC with 3% methanol in chloroform
  6. customthe monoadducts were separated by repetitive developments with 3% methanol in chloroform

Sources & evidence

ORD record
ord-71dbd280918247aa880e3098511eb6c2
Source dataset
uspto-grants-2001_09
Patent number
US06284258B1

Reaction notes

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