Acetic Acid → HCID 21023943, compound

HRID 1795675Notes

Reaction equation

HRID 1795675 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH:11]1[C:12]([OH:58])([CH3:57])[CH2:13][CH2:14][CH:15]([O:49][Si:50]([C:53]([CH3:56])([CH3:55])[CH3:54])([CH3:52])[CH3:51])[CH2:16][C:17]([O:19][CH:20](/[C:25](/[CH3:48])=[CH:26]/[CH:27]=[CH:28]/[CH:29]([CH3:47])[CH2:30][CH:31]2[O:46][CH:32]2[CH:33]([CH3:45])[CH:34]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH2:35][CH3:36])[CH:21]([CH3:24])[CH:22]=[CH:23]1)=[O:18])(=O)C.C(O)(=O)C>>[O:49]([CH:15]1[CH2:14][CH2:13][C:12]([OH:58])([CH3:57])[CH:11]([OH:10])[CH:23]=[CH:22][CH:21]([CH3:24])[CH:20](/[C:25](/[CH3:48])=[CH:26]/[CH:27]=[CH:28]/[CH:29]([CH3:47])[CH2:30][CH:31]2[O:46][CH:32]2[CH:33]([CH3:45])[CH:34]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH2:35][CH3:36])[O:19][C:17](=[O:18])[CH2:16]1)[Si:50]([C:53]([CH3:56])([CH3:55])[CH3:54])([CH3:52])[CH3:51]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 21023995HCID 21023995, compound

Product 1

HCID 21023943HCID 21023943, compoundYield 95.4%

Procedure

Potassium carbonate (48 mg, 0.35 mmol) was added to a solution of (8E,12E,14E)-7-acetoxy-3,21-bis(t-butyldimethylsiloxy)-6-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (220 mg, 0.29 mmol) obtained in Example B11 methanol (15 mL), followed by stirring at room temperature for 15 hours. After acetic acid (40 μL, 0.69 mmol) was added, the reaction solution was evaporated. The residue was dissolved in ethyl acetate, and the solution was washed with a saturated sodium bicarbonate aqueous solution and brine, dried over anhydrous magnesium sulfate and then concentrated to dryness under reduced pressure to obtain the title compound (0.2 g, 95%) as a colorless amorphous.

Workup

  1. customthe reaction solution was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe solution was washed with a saturated sodium bicarbonate aqueous solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1df35242aca44522a43758aea03d1b3b
Source dataset
uspto-grants-2006_04
Patent number
US07026352B1

Reaction notes

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