Methanol → HCID 23362223, compound

HRID 1082113Notes

Reaction equation

HRID 1082113 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([S:27][CH3:28])[C:23]([O:25]C)=[O:24])=[CH:17][CH:16]=1)[CH3:11].[OH-].[Na+].CO>O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([S:27][CH3:28])[C:23]([OH:25])=[O:24])=[CH:17][CH:16]=1)[CH3:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 23362228HCID 23362228, compound

Product 1

HCID 23362223HCID 23362223, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-(methylthio)propanoate (1.01 g), 10% aqueous sodium hydroxide solution (10 mL) and methanol (20 mL) was heated at reflux for 1 hour. The mixture was diluted with water (300 mL) and washed with dichloromethane (3×200 mL). The aqueous layer was acidified to pH2 with concentrated hydrochloric acid, extracted with ethyl acetate (3×200 mL) and the extracts washed with brine (2×200 mL), dried (MgSO4) and evaporated. The residue was chromatographed on silica gel with 2% methanol in dichloromethane as eluent to afford the title compound, mp 140°-1° C. (ethyl acetate-hexane).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. washwashed with dichloromethane (3×200 mL)
  4. extractionextracted with ethyl acetate (3×200 mL)
  5. washthe extracts washed with brine (2×200 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was chromatographed on silica gel with 2% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-075d32aa6e6e4728b4a21859751898c7
Source dataset
uspto-grants-1996_12
Patent number
US05589492

Reaction notes

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