Methanol → HCID 23362229, compound

HRID 1082109Notes

Reaction equation

HRID 1082109 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]([Cl:27])[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]([Cl:27])[C:23]([OH:25])=[O:24])=[CH:17][CH:16]=1)[CH3:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 15186152HCID 15186152, compound

Product 1

HCID 23362229HCID 23362229, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-chloropropanoate (0.94 g), 10% aqueous sodium hydroxide solution (5 mL) and methanol (15 mL) was stirred at room temperature for 1.75 hrs. The mixture was then diluted with water (400 mL) and washed with dichloromethane (300 mL). The aqueous layer was acidified to pH 2 with concentrated hydrochloric acid and extracted with ethyl acetate (2×250 mL). The combined ethyl acetate extracts were washed with water (500 mL), brine (500 mL), dried (MgSO4) and evaporated. The residue was crystallised from dichloromethane-hexane to afford the title compound, mp 142°-3° C.

Workup

  1. washwashed with dichloromethane (300 mL)
  2. extractionextracted with ethyl acetate (2×250 mL)
  3. washThe combined ethyl acetate extracts were washed with water (500 mL), brine (500 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was crystallised from dichloromethane-hexane

Sources & evidence

ORD record
ord-e23d0b17de77424b9aa58e1762378c6f
Source dataset
uspto-grants-1996_12
Patent number
US05589492

Reaction notes

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