Hydrochloric Acid → HCID 131725087, compound

HRID 586669Notes

Reaction equation

HRID 586669 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([CH3:33])[C:19]1[CH:28]=[CH:27][C:26]2[C:25]([CH3:30])([CH3:29])[CH2:24][CH2:23][C:22]([CH3:32])([CH3:31])[C:21]=2[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([CH3:33])[C:19]1[CH:28]=[CH:27][C:26]2[C:25]([CH3:30])([CH3:29])[CH2:24][CH2:23][C:22]([CH3:32])([CH3:31])[C:21]=2[CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131725081HCID 131725081, compound

Product 1

HCID 131725087HCID 131725087, compoundYield 83.4%

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 16a (59 mg, 0.13 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) ad 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 (43 mg, 79% 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-6c49ac6d05fb4a7cae2613cc15fc3ab4
Source dataset
uspto-grants-2005_08
Patent number
US06936636B2

Reaction notes

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