Methanol → HCID 18794804, compound

HRID 400117Notes

Reaction equation

HRID 400117 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]([O:28][CH3:29])[C:23]([O:25]CC)=[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]([O:28][CH3:29])[C:23]([OH:25])=[O:24])=[CH:17][CH:16]=1)[CH3:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 18794789HCID 18794789, compound

Product 1

HCID 18794804HCID 18794804, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino)ethoxy]-phenyl]-2-methoxypropanoate (1.5 g), 10% aqueous sodium hydroxide solution (7.5 mL) and methanol (23 mL) was stirred for 1.5 hrs at room temperature and then diluted with water (600 mL), washed with dichloromethane (300 mL) and acidified to pH2 with concentrated hydrochloric acid. The mixture was extracted with ethyl acetate (3×300 mL) and the combined ethyl acetate solutions washed with water (2×200 mL) and brine (200 mL), dried (MgSO4) and evaporated. The residue was crystallised from ethyl acetate-dichloromethane-hexane to afford the title compound, mp 150°-153° C.

Workup

  1. washwashed with dichloromethane (300 mL)
  2. extractionThe mixture was extracted with ethyl acetate (3×300 mL)
  3. washthe combined ethyl acetate solutions washed with water (2×200 mL) and brine (200 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was crystallised from ethyl acetate-dichloromethane-hexane

Sources & evidence

ORD record
ord-03531bbe66804130986463175a49fd70
Source dataset
uspto-grants-1998_10
Patent number
US05827865

Reaction notes

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