Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 21023988, compound

HRID 1446633Notes

Reaction equation

HRID 1446633 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[C:18]([O:21][CH:22]1[C:23]([O:61]C(OCC)C)([CH3:60])[CH2:24][CH2:25][CH:26]([OH:59])[CH2:27][C:28]([O:30][CH:31](/[C:36](/[CH3:58])=[CH:37]/[CH:38]=[CH:39]/[CH:40]([CH3:57])[CH2:41][CH:42]2[O:56][CH:43]2[CH:44]([CH3:55])[CH:45]([O:48][C:49](=[O:54])[CH2:50][O:51][CH2:52][CH3:53])[CH2:46][CH3:47])[CH:32]([CH3:35])[CH:33]=[CH:34]1)=[O:29])(=[O:20])[CH3:19]>CO.C(OCC)(=O)C>[C:18]([O:21][CH:22]1[C:23]([OH:61])([CH3:60])[CH2:24][CH2:25][CH:26]([OH:59])[CH2:27][C:28]([O:30][CH:31](/[C:36](/[CH3:58])=[CH:37]/[CH:38]=[CH:39]/[CH:40]([CH3:57])[CH2:41][CH:42]2[O:56][CH:43]2[CH:44]([CH3:55])[CH:45]([O:48][C:49](=[O:54])[CH2:50][O:51][CH2:52][CH3:53])[CH2:46][CH3:47])[CH:32]([CH3:35])[CH:33]=[CH:34]1)=[O:29])(=[O:20])[CH3:19]

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 21023989HCID 21023989, compound

Product 1

HCID 21023988HCID 21023988, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyridinium p-toluenesulfonate (29 mg, 0.12 mmol) was added to a solution of (8E,12E,14E)-7-acetoxy-21-ethoxyacetoxy-6-(1-ethoxyethoxy)-3-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (8.0 mg, 0.012 mmol) in methanol (1.0 mL) at room temperature, followed by stirring at the same temperature for one hour. After the reaction mixture was diluted with ethyl acetate, it was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The resulting crude product was purified by thin layer chromatography (MERCK Silicagel 60 F254, 0.25 mm, developing solution; hexane:ethyl acetate=1:2) to obtain the title compound (4.0 mg, 56%) as a colorless oil.

Workup

  1. washwas washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated
  4. customThe resulting crude product was purified by thin layer chromatography (MERCK Silicagel 60 F254, 0.25 mm, developing solution; hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-a00c83f3929b432aae07797c3cac8dc1
Source dataset
uspto-grants-2010_02
Patent number
US07667052B2

Reaction notes

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