Ethyl Acetate → HCID 68153540, compound

HRID 1946926Notes

Reaction equation

HRID 1946926 reaction equation
[O:1]1CC[O:3][CH:2]1[C:6]1[CH:7]=[C:8]([C:12]2([CH3:19])[NH:17][C:16](=[O:18])[CH2:15][O:14][CH2:13]2)[CH:9]=[CH:10][CH:11]=1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].C(OCC)(=O)C>O1CCCC1.O>[CH3:19][C:12]1([C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=2)[C:2]([OH:3])=[O:1])[CH2:13][O:14][CH2:15][C:16](=[O:18])[NH:17]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24412Potassium PersulfateHCID 68153332HCID 68153332, compound

Product 1

HCID 68153540HCID 68153540, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (RS)-5-(3-[1,3]dioxolan-2-yl-phenyl)-5-methyl-morpholin-3-one (1.49 g, 5.7 mmol) in a mixture of tetrahydrofuran (65 ml) and water (13 ml) was treated with potassium monopersulphate (5.21 g, 8.5 mmol) under stirring at room temperature for 3 hours. For the workup, water (20 ml) and ethyl acetate were added. The organic layer was separated, washed with water (2×20 ml). The organic layer was dried over sodium sulphate and evaporated at reduced pressure. The 3-((RS)-3-methyl-5-oxo-morpholin-3-yl)-benzoic acid obtained (0.9 g, 67% of theory) was pure and could be used in the next step without further purification.

Workup

  1. customThe organic layer was separated
  2. washwashed with water (2×20 ml)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-9c1866058e8e426cbf4f59a5d3fc8f1a
Source dataset
uspto-grants-2013_03
Patent number
US08399459B2

Reaction notes

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