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

HRID 1795691Notes

Reaction equation

HRID 1795691 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-2af17f6d505b401d8ea661f384b42ef2
Source dataset
uspto-grants-2006_04
Patent number
US07026352B1

Reaction notes

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