Sodium Hydroxide → HCID 18172361, compound

HRID 396936Notes

Reaction equation

HRID 396936 reaction equation
[CH:1]1[C:14]2[N:13]([CH2:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:26]([O:28]C)=[O:27])=[CH:20][CH:19]=3)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[CH:11]1[C:12]2[N:13]([CH2:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([O:30][C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:26]([OH:28])=[O:27])=[CH:20][CH:19]=3)[C:14]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[O:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18172349HCID 18172349, compound

Product 1

HCID 18172361HCID 18172361, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (±) methyl 3-[4-[2-(Phenoxazin-10-yl)ethoxy]phenyl]-2-phenoxypropanoate (300 mg, 0.6 mmol) obtained in example 34 in methanol (15 mL) was added 10% NaOH solution (5 mL). The reaction was stirred at room temperature for 10 h. Methanol was removed and the residue was acidified with 2N HCl, extracted with ethylacetated (3×10 mL). The organic layer was washed with water, brine, dried and concentrated. The residue was chromatographed using 30% ethylacetate:pet, ether to afford a third liquid which was triturated with per ether to yield the title compound as a solid (192 mg, 66%). mp: 119-120° C.

Workup

  1. customMethanol was removed
  2. extractionextracted with ethylacetated (3×10 mL)
  3. washThe organic layer was washed with water, brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was chromatographed
  7. custompet, ether to afford a third liquid which
  8. customwas triturated with per ether

Sources & evidence

ORD record
ord-5b8db7270ad849cc9d027fd6b1ed3961
Source dataset
uspto-grants-2003_08
Patent number
US06608194B1

Reaction notes

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