Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 9853338, compound

HRID 2104200Notes

Reaction equation

HRID 2104200 reaction equation
[C:1]([O:9][CH:10]([CH2:63][CH3:64])[CH:11]([CH3:62])[CH:12]1[O:61][CH:13]1[CH2:14][CH:15]([CH3:60])/[CH:16]=[CH:17]/[CH:18]=[C:19](\[CH3:59])/[CH:20]1[O:32][C:30](=[O:31])[CH2:29][CH:28]([O:33][Si](CC)(CC)CC)[CH2:27][CH2:26][C:25]([O:42]C(OCC)C)([CH3:41])[CH:24]([O:48][C:49]([N:51]2[CH2:56][CH2:55][N:54]([CH3:57])[CH2:53][CH2:52]2)=[O:50])[CH:23]=[CH:22][CH:21]1[CH3:58])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[C:1]([O:9][CH:10]([CH2:63][CH3:64])[CH:11]([CH3:62])[CH:12]1[O:61][CH:13]1[CH2:14][CH:15]([CH3:60])/[CH:16]=[CH:17]/[CH:18]=[C:19](\[CH3:59])/[CH:20]1[O:32][C:30](=[O:31])[CH2:29][CH:28]([OH:33])[CH2:27][CH2:26][C:25]([OH:42])([CH3:41])[CH:24]([O:48][C:49]([N:51]2[CH2:52][CH2:53][N:54]([CH3:57])[CH2:55][CH2:56]2)=[O:50])[CH:23]=[CH:22][CH:21]1[CH3:58])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86608521HCID 86608521, compound

Product 1

HCID 9853338HCID 9853338, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(8E,12E,14E)-21-benzoyloxy-6-(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-7-((4-methylpiperazin-1-yl)carbonyl)oxy-3-triethylsiloxy-18,19-epoxytricosa-8,12,14-trien-11-olide (19.7 mg, 21.6 μmol) was dissolved in methanol (1 mL). Pyridinium p-toluenesulfonate (12.2 mg, 48.5 μmol) was added to the reaction solution at room temperature, and the reaction solution was stirred at the same temperature for 5.5 hours. The reaction solution was concentrated, and the concentrate was suspended in ethyl acetate (30 mL). This suspension was washed with a saturated aqueous solution of sodium hydrogencarbonate (6 mL) twice, purified water (6 mL) twice, and brine (6 mL). The resulting organic layer was dried over sodium sulfate, and then filtered. The filtrate was concentrated. The concentrate was purified by thin-layer chromatography (Fuji Silysia, NH Silica gel Plate; chloroform:methanol=40:1) to obtain the title compound (14.3 mg, 19.7 μmol, 91.2%) as a colorless oil.

Workup

  1. concentrationThe reaction solution was concentrated
  2. washThis suspension was washed with a saturated aqueous solution of sodium hydrogencarbonate (6 mL) twice
  3. custompurified water (6 mL) twice
  4. dry with materialThe resulting organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customThe concentrate was purified by thin-layer chromatography (Fuji Silysia, NH Silica gel Plate; chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-e622f54a10c242248acf71924793be9d
Source dataset
uspto-grants-2009_08
Patent number
US07576204B2

Reaction notes

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