Sodium Hydroxide → HCID 9930450, compound

HRID 393555Notes

Reaction equation

HRID 393555 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 (×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 (×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-9a57618f6d854c72abbaa1f0c484a7e8
Source dataset
uspto-grants-2004_10
Patent number
US06809095B2

Reaction notes

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