Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 21023949, compound

HRID 1446641Notes

Reaction equation

HRID 1446641 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(OC([O:23][CH:24]1[CH2:36][CH2:35][C:34]([O:38]C(OCC)C)([CH3:37])[CH:33]([O:44][C:45](=[O:53])[CH2:46][N:47]2[CH2:52][CH2:51][O:50][CH2:49][CH2:48]2)[CH:32]=[CH:31][CH:30]([CH3:54])[CH:29](/[C:55](/[CH3:76])=[CH:56]/[CH:57]=[CH:58]/[CH:59]([CH3:75])[CH2:60][CH:61]2[O:74][CH:62]2[CH:63]([CH3:73])[CH:64]([O:67]C(OCC)C)[CH2:65][CH3:66])[O:28][C:26](=[O:27])[CH2:25]1)C)C>CO>[OH:23][CH:24]1[CH2:36][CH2:35][C:34]([OH:38])([CH3:37])[CH:33]([O:44][C:45](=[O:53])[CH2:46][N:47]2[CH2:48][CH2:49][O:50][CH2:51][CH2:52]2)[CH:32]=[CH:31][CH:30]([CH3:54])[CH:29](/[C:55](/[CH3:76])=[CH:56]/[CH:57]=[CH:58]/[CH:59]([CH3:75])[CH2:60][CH:61]2[O:74][CH:62]2[CH:63]([CH3:73])[CH:64]([OH:67])[CH2:65][CH3:66])[O:28][C:26](=[O:27])[CH2:25]1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 21023946HCID 21023946, compound

Product 1

HCID 21023949HCID 21023949, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyridinium p-toluenesulfonate (2.2 mg, 8.71 μmol) was added to a solution of (8E,12E,14E)-3,6,21-tri(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-7-(morpholin-4-yl)acetoxy-18,19-epoxytricosa-8,12,14-trien-11-olide (7.3 mg, 8.71 μmol) in methanol (1 mL), followed by stirring at room temperature overnight. The reaction solution was evaporated, and to the resulting residue were added ethyl acetate, water and a saturated sodium bicarbonate aqueous solution. The mixture was extracted with ethyl acetate, and the resulting organic layer was dried over anhydrous magnesium sulfate, filtered and then evaporated. The resulting residue was purified by thin layer chromatography (MERCK Silica gel 60 F254, 0.2 mm, developing solution; methanol-dichloromethane=1:19) to obtain the title compound (4.4 mg, 82%) as a colorless oil.

Workup

  1. customThe reaction solution was evaporated
  2. additionto the resulting residue were added ethyl acetate, water
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe resulting organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting residue was purified by thin layer chromatography (MERCK Silica gel 60 F254, 0.2 mm, developing solution; methanol-dichloromethane=1:19)

Sources & evidence

ORD record
ord-fd592f6193554f52a52b5e6b27d4bd79
Source dataset
uspto-grants-2010_02
Patent number
US07667052B2

Reaction notes

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