Acetic Acid → HCID 57742193, compound

HRID 660329Notes

Reaction equation

HRID 660329 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-ac1cc2cdfa934351b34aae9eb9055f4c
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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