Acetic Acid → HCID 57742193, compound

HRID 1626886Notes

Reaction equation

HRID 1626886 reaction equation
C([O:3][C:4](=[O:17])[CH:5]([C:7]1[CH:16]=[CH:15][C:10]2[NH:11][CH2:12][CH2:13][O:14][C:9]=2[CH:8]=1)[CH3:6])C.[OH-].[Na+].CC(O)=O>C1COCC1.O>[O:14]1[C:9]2[CH:8]=[C:7]([CH:5]([CH3:6])[C:4]([OH:17])=[O:3])[CH:16]=[CH:15][C:10]=2[NH:11][CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 57742146HCID 57742146, compound

Product 1

HCID 57742193HCID 57742193, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(3,4-dihydro-2H-benzo[1,4]oxazin-7-yl)-propionic acid ethyl ester (258 mg) in THF (3 mL) and H2O (3 mL) was added NaOH (134 mg) at room temperature. After being stirred for 20 h at room temperature, the reaction mixture was acidified with AcOH (pH=4) and diluted with water. The resulting mixture extracted with dichloromethane and the combined organic layer was dried magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was chromatographed on silica gel (CH2Cl2:MeOH=15:1) to afford the product as a brown oil. (150 mg, 65.8%)

Workup

  1. extractionThe resulting mixture extracted with dichloromethane
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was chromatographed on silica gel (CH2Cl2:MeOH=15:1)

Sources & evidence

ORD record
ord-5cc0a24bc25a4fcc8ba1b0c3a2717243
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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