Hydrochloric Acid → HCID 58304033, compound

HRID 1404142Notes

Reaction equation

HRID 1404142 reaction equation
[F:1][C:2]1[C:3]([OH:15])=[C:4]2C(=[CH:9][CH:10]=1)NC=[C:5]2[CH2:11][C:12]([OH:14])=[O:13].[OH-].[K+].[CH3:18]I.[OH-].[Na+].Cl.[CH3:23][N:24]([CH:26]=O)[CH3:25]>CO.C(OCC)(=O)C.O>[F:1][C:2]1[C:3]([O:15][CH3:18])=[C:4]2[C:25](=[CH:9][CH:10]=1)[N:24]([CH3:23])[CH:26]=[C:5]2[CH2:11][C:12]([OH:14])=[O:13]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 58303991HCID 58303991, compound

Product 1

HCID 58304033HCID 58304033, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of compound 34-3 (1 g, 4.78 mmol), KOH (1 g, 19.14 mmol), MeI (2.7 g, 19.14 mmol) in DMF (20 mL) was stirred at room temperature for 2 h. Water (50 mL) and ethyl acetate (50 mL) were added to the mixture. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×30 mL). The organic layers were combined, dried over MgSO4, filtered, and evaporated to afford crude product (600 mg). To this crude product was added methanol (10 mL) and NaOH aq. (2 N, 8 mL) and then the reaction mixture was stirred and refluxed for 1 h. The mixture was allowed to cool to room temperature and neutralized with hydrochloric acid to pH=7 before it was extracted with ethyl acetate (2×30 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated under reduce pressure to afford 34-4 (250 mg, 85%) as yellow oil. LRMS: calc 237.2 and found: 238.1 [M+1].

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×30 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto afford crude product (600 mg)
  7. stirringthe reaction mixture was stirred
  8. temperaturerefluxed for 1 h
  9. extractionwas extracted with ethyl acetate (2×30 mL)
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-0dab4fb9011e44438096db1c0526a2e0
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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