Potassium Carbonate → 12-Allyl-5,17-dihydroxy-19-[4-hydroxy-3-methoxycyclo hexyl]-13-oxo-2,8,10,16,18-pentamethyl-4,6-dimethoxynona deca-10.18-dienoic acid

HRID 248449Notes

Reaction equation

HRID 248449 reaction equation
[CH2:1]([CH:4]1[CH:30]=[C:29]([CH3:31])[CH2:28][CH:27]([CH3:32])[CH2:26][CH:25]([O:33][CH3:34])[CH:24]2[O:35][C:20](O)([CH:21](C)[CH2:22][CH:23]2[O:36][CH3:37])C(O)C(=O)N2C(CCCC2)C(=O)[O:10][CH:9]([C:43]([CH3:54])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([OH:51])[CH:47]([O:52][CH3:53])[CH2:46]2)[CH:8]([CH3:55])[CH2:7][CH2:6][C:5]1=[O:56])[CH:2]=[CH2:3].[C:57](=[O:60])([O-])[O-:58].[K+].[K+]>CO>[CH2:1]([CH:4]([C:5](=[O:56])[CH2:6][CH2:7][CH:8]([CH3:55])[CH:9]([OH:10])[C:43]([CH3:54])=[CH:44][CH:45]1[CH2:50][CH2:49][CH:48]([OH:51])[CH:47]([O:52][CH3:53])[CH2:46]1)[CH:30]=[C:29]([CH3:31])[CH2:28][CH:27]([CH3:32])[CH2:26][CH:25]([O:33][CH3:34])[CH:24]([OH:35])[CH:23]([O:36][CH3:37])[CH2:22][CH:21]([CH3:20])[C:57]([OH:58])=[O:60])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57281065HCID 57281065, compound

Product 1

HCID 5698545312-Allyl-5,17-dihydroxy-19-[4-hydroxy-3-methoxycyclo hexyl]-13-oxo-2,8,10,16,18-pentamethyl-4,6-dimethoxynona deca-10.18-dienoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 17-allyl-1,2-dihydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo [22.3.1.04,9 ]octacos-18-ene-3,10,16-trione (the compound of Example 15, European Patent Application No 323042) (2.5 g) and potassium carbonate (1.14 g) in methanol (25 ml) was stirred at ambient temperature for 1.5 hours, and then filtered. To the filtrate were added water and diethyl ether, and the separated aqueous layer was acidified with 1N hydrochloric acid. The precipitate was extracted with diethyl ether and the extract was washed with brine, dried and then concentrated in vacuo to give the crude subtitle compound.

Workup

  1. filtrationfiltered
  2. additionTo the filtrate were added water and diethyl ether
  3. extractionThe precipitate was extracted with diethyl ether
  4. washthe extract was washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1948c8ee43834feda175d0176632835e
Source dataset
uspto-grants-1993_05
Patent number
US05210227

Reaction notes

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