Ethyl Acetate → HCID 56609779, compound

HRID 2288075Notes

Reaction equation

HRID 2288075 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C:17]23[C:28]4([CH:30]=[O:31])[CH2:29][CH:20]([C:21]2([CH2:33][O:34][C:35]25[CH:46]([O:47][Si](C(C)(C)C)(C)C)[CH:41]6[CH:42]([O:43][CH2:44][CH3:45])[CH:37]([CH:38]([O:40]6)[O:39]2)[O:36]5)[CH2:22][CH:23]2[CH:27]4[CH2:26][CH2:25][CH:24]2[CH3:32])[CH:19]=[C:18]3[CH:55]([CH3:57])[CH3:56])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OCC)(=O)C>[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[C:1]1([CH:7]([O:14][C:15]([C:17]23[C:28]4([CH:30]=[O:31])[CH2:29][CH:20]([C:21]2([CH2:33][O:34][C:35]25[CH:46]([OH:47])[CH:41]6[CH:42]([O:43][CH2:44][CH3:45])[CH:37]([CH:38]([O:40]6)[O:39]2)[O:36]5)[CH2:22][CH:23]2[CH:27]4[CH2:26][CH2:25][CH:24]2[CH3:32])[CH:19]=[C:18]3[CH:55]([CH3:56])[CH3:57])=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 57122860HCID 57122860, compound

Product 1

HCID 56609779HCID 56609779, compound

Reagents, catalysts & solvents 1

HCID 11078149TBAF tetrahydrofuranSolvent

Procedure

Compound (27) was mixed with in 70 μl of 1M tetrabutylammonium fluoride-tetrahydrofuran solution and stirred at room temperature. After 80 minutes, the reaction solution was mixed with 15 ml of ethyl acetate and washed with 10 ml of sodium phosphate buffer (10 mM, pH 5.97) and then with 10 ml of water twice. After the washing, the ethyl acetate layer was dried over anhydrous sodium sulfate, filtered for removal of solids and concentrated in vacuo to give a crude reaction product. The reaction product was further subjected to silica gel column chromatography (Kieselgel 60, Merck, 1.5φ×15 cm) and eluted with n-hexane-ethyl acetate (3:1) to give 21.2 mg of compound (28) as a colorless oily substance.

Workup

  1. washwashed with 10 ml of sodium phosphate buffer (10 mM, pH 5.97)
  2. dry with materialAfter the washing, the ethyl acetate layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered for removal of solids
  4. concentrationconcentrated in vacuo
  5. customto give a crude
  6. customreaction product
  7. washeluted with n-hexane-ethyl acetate (3:1)

Sources & evidence

ORD record
ord-caceb061c69644cb97ce902cc71faea2
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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