Sodium Hydroxide → HCID 11141777, compound

HRID 377566Notes

Reaction equation

HRID 377566 reaction equation
[OH-].[Na+].[CH3:3][S:4][CH2:5][C:6]1[O:11][CH2:10][N:9]([C:12]([CH3:19])([CH3:18])[C:13]([O:15]CC)=[O:14])[C:8](=[O:20])[C:7]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)C.O1CCOCC1.O>[CH3:3][S:4][CH2:5][C:6]1[O:11][CH2:10][N:9]([C:12]([CH3:19])([CH3:18])[C:13]([OH:15])=[O:14])[C:8](=[O:20])[C:7]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 19354572HCID 19354572, compound

Product 1

HCID 11141777HCID 11141777, compoundYield 38.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of sodium hydroxide (16.43 g) in 10 water was added to a stirred solution of ethyl 2-(2,3-dihydro-6-methylthiomethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (68 g) in a mixture of ethanol and 1,4-dioxan. The solution was heated at 60° C. for 6 hours, allowed to cool and the solvent was removed under reduced pressure to give an orange oil which was dissolved in water. The aqueous solution was washed with dichloromethane, acidified to pH 1 with concentrated hydrochloric acid, extracted with dichloromethane, the extract dried (magnesium sulphate) and evaporated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with dichloromethane/ethyl acetate to give 2-(2,3-dihydro-6-methylthiomethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoic acid (24.2 g) as a yellow solid, m.p. 136-137° C.

Workup

  1. temperatureto cool
  2. customthe solvent was removed under reduced pressure
  3. customto give an orange oil which
  4. washThe aqueous solution was washed with dichloromethane
  5. extractionextracted with dichloromethane
  6. dry with materialthe extract dried (magnesium sulphate)
  7. customevaporated under reduced pressure
  8. customThe residue was purified by chromatography on silica gel
  9. washeluting with dichloromethane/ethyl acetate

Sources & evidence

ORD record
ord-58038c6d686241d8b1c4fd33627180f6
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

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