Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 10031817, compound

HRID 854200Notes

Reaction equation

HRID 854200 reaction equation
C(OC([O:6][CH:7]1[CH2:19][CH2:18][CH:17]([CH3:20])[CH:16]([O:21][C:22]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[O:23])[CH:15]=[CH:14][CH:13]([CH3:31])[CH:12](/[C:32](/[CH3:59])=[CH:33]/[CH:34]=[CH:35]/[C:36]([O:53]C(OCC)C)([CH3:52])[CH2:37][CH:38]2[O:51][CH:39]2[CH:40]([CH3:50])[CH:41]([O:44]C(OCC)C)[CH2:42][CH3:43])[O:11][C:9](=[O:10])[CH2:8]1)C)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>O1CCCC1.CC(C)CO.C(OCC)(=O)C>[OH:6][CH:7]1[CH2:19][CH2:18][CH:17]([CH3:20])[CH:16]([O:21][C:22]([N:24]2[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]2)=[O:23])[CH:15]=[CH:14][CH:13]([CH3:31])[CH:12](/[C:32](/[CH3:59])=[CH:33]/[CH:34]=[CH:35]/[C:36]([OH:53])([CH3:52])[CH2:37][CH:38]2[O:51][CH:39]2[CH:40]([CH3:50])[CH:41]([OH:44])[CH2:42][CH3:43])[O:11][C:9](=[O:10])[CH2:8]1

Participants

6

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2×HCID 86601411HCID 86601411, compound

Product 1

HCID 10031817HCID 10031817, compoundYield 65.4%

Reagents, catalysts & solvents 3

HCID 6560IsobutanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(8E,12E,14E)-3,16,21-tris-(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-7-((4-methylpiperazin-1-yl)carbonyl)oxy-18,19-epoxytricosa-8,12,14-trien-11-olide (25.1 mg, 30.0 limol) was dissolved in a 1:1 mixed solution of tetrahydrofuran and 2-methyl-1-propanol (1 mL). Pyridinium p-toluenesulfonate (23.7 mg, 94.3 μmol) was added to the reaction mixture at room temperature. The reaction mixture was stirred at the same temperature for 24.5 hours, and then pyridinium p-toluenesulfonate (8.7 mg, 34.6 μmol) was further added to the reaction mixture. The reaction mixture was stirred for 4.5 hours. The reaction mixture was diluted with ethyl acetate (30 mL), and the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (6 mL) and purified water (6 mL) twice, and with brine (6 mL). The resulting organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The resulting concentrate was purified by thin-layer chromatography (Fuji Silysia NH Silica gel plate; chloroform:methanol=40:1) to obtain the title compound (12.2 mg, 19.6 μmol, 65.3%) as a colorless oil.

Workup

  1. stirringThe reaction mixture was stirred for 4.5 hours
  2. washthe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (6 mL)
  3. custompurified water (6 mL) twice
  4. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. concentrationThe resulting concentrate
  8. customwas purified by thin-layer chromatography (Fuji Silysia NH Silica gel plate; chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-50f94b9ea74349f2b5406ad2e3308f83
Source dataset
uspto-grants-2007_08
Patent number
US07256178B2

Reaction notes

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