Hydrochloric Acid → HCID 23147238, compound

HRID 495302Notes

Reaction equation

HRID 495302 reaction equation
[OH:1][C:2]1[C:3]([C:14]2[O:15][C:16]([CH2:19][CH2:20][C:21](=[O:23])[CH3:22])=[CH:17][CH:18]=2)=[C:4]([CH2:9][C:10]([O:12]C)=[O:11])[CH:5]=[C:6]([OH:8])[CH:7]=1.[OH-].[Na+].Cl>C(#N)C>[OH:1][C:2]1[C:3]([C:14]2[O:15][C:16]([CH2:19][CH2:20][C:21](=[O:23])[CH3:22])=[CH:17][CH:18]=2)=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[C:6]([OH:8])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23146927HCID 23146927, compound

Product 1

HCID 23147238HCID 23147238, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Compound 261 (20 mg, 0.063 mmol) obtained in Example 261 was dissolved in acetonitrile (2.0 mL), and aqueous 4 mol/L sodium hydroxide solution (2.0 mL, 4.0 mmol) was added thereto and stirred at 60° C. for 3 hours. 3 mol/L hydrochloric acid (4.0 mL) was added to the reaction solution, and extracted twice with chloroform (50 mL). The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through preparative thin-layer chromatography (methanol/chloroform=1/6) to obtain Compound 262 (10 mg, 52%).

Workup

  1. extractionextracted twice with chloroform (50 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated away under reduced pressure
  4. customThe resulting residue was purified through preparative thin-layer chromatography (methanol/chloroform=1/6)

Sources & evidence

ORD record
ord-a06c6883797f48aa9400108f06bf74d8
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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