HCID 58932261, compound → HCID 58932232, compound

HRID 854206Notes

Reaction equation

HRID 854206 reaction equation
NC(N)=N.[N+]([O-])(O)=O.NC(N)=N.C([O:16][CH:17]1[CH:18]([CH3:66])[CH2:19][CH2:20][CH:21]([O:57][Si:58]([CH2:64][CH3:65])([CH2:62][CH3:63])[CH:59]([CH3:61])[CH3:60])[CH2:22][C:23]([O:25][CH:26](/[C:31](/[CH3:56])=[CH:32]/[CH:33]=[CH:34]/[C:35]([OH:55])([CH3:54])[CH2:36][CH:37]2[O:53][CH:38]2[CH:39]([CH3:52])[CH:40]([O:43][Si:44]([CH2:50][CH3:51])([CH2:48][CH3:49])[CH:45]([CH3:47])[CH3:46])[CH2:41][CH3:42])[CH:27]([CH3:30])[CH:28]=[CH:29]1)=[O:24])(=O)C>C(OCC)(=O)C>[CH2:64]([Si:58]([CH2:62][CH3:63])([CH:59]([CH3:60])[CH3:61])[O:57][CH:21]1[CH2:20][CH2:19][CH:18]([CH3:66])[CH:17]([OH:16])[CH:29]=[CH:28][CH:27]([CH3:30])[CH:26](/[C:31](/[CH3:56])=[CH:32]/[CH:33]=[CH:34]/[C:35]([OH:55])([CH3:54])[CH2:36][CH:37]2[O:53][CH:38]2[CH:39]([CH3:52])[CH:40]([O:43][Si:44]([CH2:48][CH3:49])([CH2:50][CH3:51])[CH:45]([CH3:47])[CH3:46])[CH2:41][CH3:42])[O:25][C:23](=[O:24])[CH2:22]1)[CH3:65]

Participants

4

Reactant 2

HCID 58932261HCID 58932261, compoundHCID 86601416HCID 86601416, compound

Product 1

HCID 58932232HCID 58932232, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 0.2M guanidine/guanidine nitrate solution (methanol-methylene chloride, 9:1)(3.9 mL, 0.78 mmol) was added to (8E,12E,14E)-7-acetoxy-3,21-bis(diethylisopropylsiloxy)-16-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (307 mg, 0.3868 mmol), and the reaction mixture was stirred at room temperature for 13 hours. The reaction mixture was diluted with ethyl acetate, and then the organic layer was washed with an aqueous solution of ammonium chloride. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane, 1:4) to obtain the title compound (271.5 mg, 93%) as a colorless oil.

Workup

  1. washthe organic layer was washed with an aqueous solution of ammonium chloride
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane, 1:4)

Sources & evidence

ORD record
ord-c7b4c70024554dab95cfa7da8d9a8ba3
Source dataset
uspto-grants-2007_08
Patent number
US07256178B2

Reaction notes

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