Potassium Carbonate → benzyl 2-(2,3-dihydro-6-hydroxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate

HRID 377570Notes

Reaction equation

HRID 377570 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][C:12]1[O:17][CH2:16][N:15]([C:18]([CH3:30])([CH3:29])[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[C:14](=[O:31])[C:13]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=O)C>O.CO>[OH:10][CH2:11][C:12]1[O:17][CH2:16][N:15]([C:18]([CH3:30])([CH3:29])[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[C:14](=[O:31])[C:13]=1[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 19354621benzyl 2-(6-acetoxymethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate

Product 1

HCID 19354618benzyl 2-(2,3-dihydro-6-hydroxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoateYield 103.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium carbonate (0.96 g) in water was added in portions to a stirred solution of benzyl 2-(6-acetoxymethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (2.70 g) in methanol at 0° C. The mixture was stirred at ambient temperature for 1 hour and the solvent was evaporated under reduced pressure. The residue was acidified with 2 M hydrochloric acid, extracted with diethyl ether, the extract was dried (magnesium sulphate) and the solvent evaporated under reduced pressure to give benzyl 2-(2,3-dihydro-6-hydroxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (2.51 g) as a yellow gum, NMR (CDCl3) 1.6(s,6H), 4.15(s,2H), 5.1(s,2H), 5.3(s,2H), 7.26-7.42(m,10H).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. extractionextracted with diethyl ether
  3. dry with materialthe extract was dried (magnesium sulphate)
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-b0c513d3445c40e39356cd76a9895888
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

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