Hydrochloric Acid → HCID 131725099, compound

HRID 586692Notes

Reaction equation

HRID 586692 reaction equation
[OH-].[Na+].[CH3:3][O:4][CH2:5][C@@H:6]1[C@H:8](/[CH:9]=[CH:10]/[C:11](/[CH3:18])=[CH:12]/[C:13]([O:15]CC)=[O:14])[C@@:7]1([CH3:31])[C:19]1[CH:24]=[C:23]([CH:25]([CH3:27])[CH3:26])[CH:22]=[C:21]([CH:28]([CH3:30])[CH3:29])[CH:20]=1.Cl>C1COCC1.CO.C(OCC)(=O)C>[CH3:3][O:4][CH2:5][C@@H:6]1[C@H:8](/[CH:9]=[CH:10]/[C:11](/[CH3:18])=[CH:12]/[C:13]([OH:15])=[O:14])[C@@:7]1([CH3:31])[C:19]1[CH:20]=[C:21]([CH:28]([CH3:29])[CH3:30])[CH:22]=[C:23]([CH:25]([CH3:27])[CH3:26])[CH:24]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131725094HCID 131725094, compound

Product 1

HCID 131725099HCID 131725099, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydroxide solution (1N, 1 mL) was added to a solution of Compound 24 (20 mg, 0.05 mmol) in 4 mL of THF/MeOH (1:1) at 50° C. After stirring at 50° C. for 16 h, the mixture was diluted with ethyl acetate (10 mL) and acidified with 1 mL of 1 HCl at 0° C. The organic layer was then washed with brine (1×5 mL), dried (Na2SO4) and concentrated. The residue was purified by flash chromatography using 30% EtOAc in hexane to give the title compound (17 mg, 91% yield) as a white solid:

Workup

  1. washThe organic layer was then washed with brine (1×5 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-0389bac8bca849aea732965529fb0422
Source dataset
uspto-grants-2005_08
Patent number
US06936636B2

Reaction notes

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