Sodium Hydroxide → HCID 9930450, compound

HRID 1760934Notes

Reaction equation

HRID 1760934 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([O:26][CH2:27][CH3:28])[C:22]([O:24]C)=[O:23])=[CH:16][CH:15]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][CH:21]([O:26][CH2:27][CH3:28])[C:22]([OH:24])=[O:23])=[CH:18][CH:19]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9843104HCID 9843104, compound

Product 1

HCID 9930450HCID 9930450, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of methyl 3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-ethoxy propanoate (4.7 g, 12.2 mmol) obtained in example 2 in methanol (50 mL) was added aqueous 10% sodium hydroxide (28 mL). The mixture was stirred at 25° C. for 3h. The solvent was removed under reduced pressure and the residue was acidified with 2N hydrochloric acid extracted with ethyl acetate (2×100 mL). The combined ethyl acetate layers were washed with water (75 mL), brine (50 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was chromatographed over silica gel using ethyl acetate to give the title compound (3.0 g, 66%) as a syrupy liquid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washThe combined ethyl acetate layers were washed with water (75 mL), brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-588a7beac73448cd9c513f2c09ce7c70
Source dataset
uspto-grants-2005_01
Patent number
US06846824B2

Reaction notes

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