Hydrochloric Acid → HCID 13935263, compound

HRID 1493648Notes

Reaction equation

HRID 1493648 reaction equation
[Br:1]/[C:2](/[C@@H:22]([OH:30])[C@@H:23]([CH3:29])[CH2:24][C:25]#[C:26][CH2:27][CH3:28])=[CH:3]/[C@@H:4]1[C@H:11]([O:12]C(=O)C2C=CC=CC=2)[CH2:10][C@H:9]2[C@@H:5]1[CH2:6][C:7](=[O:21])[O:8]2.C(=O)([O-])[O-].[K+].[K+].Cl>CO>[Br:1]/[C:2](/[C@@H:22]([OH:30])[C@@H:23]([CH3:29])[CH2:24][C:25]#[C:26][CH2:27][CH3:28])=[CH:3]/[C@@H:4]1[C@H:11]([OH:12])[CH2:10][C@H:9]2[C@@H:5]1[CH2:6][C:7](=[O:21])[O:8]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 13935260HCID 13935260, compound

Product 1

HCID 13935263HCID 13935263, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

3.12 g of (1S,5R,6R,7R)-6-[(E)-(3S,4S)-2-bromo-3-hydroxy-4-methyl-non-1-en-6-inyl]-7-benzoyloxy-2-oxa-bicyclo[3.3.0]octan-3-one was dissolved in 18 ml of p.A. methanol, mixed with 290 mg of a finely powdered potassium carbonate and stirred for 3 h at 25° C. It was adjusted to pH 7 by addition of a 50% hydrochloric acid and concentrated by evaporation in a water-jet vacuum at 30° C. The residue was taken up in methylene chloride, filtered over magnesium sulfate and Celite, again concentrated by evaporation in a water-jet vacuum and chromatographed under pressure on about 200 ml of fine silica gel using a gradient of hexane/ethyl acetate. 2.00 g (82%) of the title compound was isolated as colorless oil.

Workup

  1. concentrationconcentrated by evaporation in a water-jet vacuum at 30° C
  2. filtrationfiltered over magnesium sulfate and Celite
  3. concentrationagain concentrated by evaporation in a water-jet vacuum
  4. customchromatographed under pressure on about 200 ml of fine silica gel using a gradient of hexane/ethyl acetate

Sources & evidence

ORD record
ord-9a22df92f79245cbadd2723f71265ebf
Source dataset
uspto-grants-1991_06
Patent number
US05023273

Reaction notes

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