Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 21024013, compound

HRID 1446629Notes

Reaction equation

HRID 1446629 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:66]C(OCC)C)([CH3:65])[CH2:24][CH2:25][CH:26]([O:58][C:59](=[O:64])[CH2:60][O:61][CH2:62][CH3:63])[CH2:27][C:28]([O:30][CH:31](/[C:36](/[CH3:57])=[CH:37]/[CH:38]=[CH:39]/[CH:40]([CH3:56])[CH2:41][CH:42]2[O:55][CH:43]2[CH:44]([CH3:54])[CH:45]([O:48]C(OCC)C)[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:66])([CH3:65])[CH2:24][CH2:25][CH:26]([O:58][C:59](=[O:64])[CH2:60][O:61][CH2:62][CH3:63])[CH2:27][C:28]([O:30][CH:31](/[C:36](/[CH3:57])=[CH:37]/[CH:38]=[CH:39]/[CH:40]([CH3:56])[CH2:41][CH:42]2[O:55][CH:43]2[CH:44]([CH3:54])[CH:45]([OH:48])[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 21024012HCID 21024012, compound

Product 1

HCID 21024013HCID 21024013, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyridinium p-toluenesulfonate (9.8 mg, 0.039 mmol) was added to a solution of (8E,12E,14E)-7-acetoxy-3-ethoxyacetoxy-6,21-bis(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (6.0 mg, 0.0078 mmol) in methanol (1.0 mL) at room temperature, followed by stirring at the same temperature for 15 hours. The reaction mixture was diluted with 15 mL of ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and evaporated. The resulting crude product was purified by thin layer chromatography (MERCK Silicagel 60 F254, 0.2 mm, developing solution; ethyl acetate) to obtain the title compound (1.7 mg, 35%) as a colorless oil.

Workup

  1. washwashed 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, 0.2 mm, developing solution; ethyl acetate)

Sources & evidence

ORD record
ord-725df7e99bd349c8ad916e31e4e3a27f
Source dataset
uspto-grants-2010_02
Patent number
US07667052B2

Reaction notes

Loading…