Chromic Acid → 2-(4-Acetamidobenzenesulphonyl)-3-carboxy-3,6-dihydro-6-(4-ethoxyphenyl)-5-methyl-2H-1,2-oxazine

HRID 1018480

Reaction equation

HRID 1018480 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH:19]([CH2:20][OH:21])[CH:18]=[C:17]([CH3:22])[CH:16]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH3:31])=[CH:25][CH:24]=3)[O:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Cr](O)(O)(=O)=[O:33].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CC(C)=O>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:14]2[CH:19]([C:20]([OH:33])=[O:21])[CH:18]=[C:17]([CH3:22])[CH:16]([C:23]3[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH3:31])=[CH:27][CH:28]=3)[O:15]2)(=[O:12])=[O:13])=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24425Chromic Acid2×HCID 656671Sodium PyrosulfiteHCID 184015412-(4-acetamidobenzenesulphonyl)-3,6-dihydro-6-(4-ethoxyphenyl)-3-hydroxymethyl-5-methyl-2H-1,2-oxazine

Product 1

HCID 98470732-(4-Acetamidobenzenesulphonyl)-3-carboxy-3,6-dihydro-6-(4-ethoxyphenyl)-5-methyl-2H-1,2-oxazine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 2-(4-acetamidobenzenesulphonyl)-3,6-dihydro-6-(4-ethoxyphenyl)-3-hydroxymethyl-5-methyl-2H-1,2-oxazine (1.02 g, 2.28 mmol) in acetone (20 ml) at 10° C. was added a solution of aaueous chromic acid (8M, 1.2 ml) dropwise. Stirred at room temperature for 2.5 h with addition of aqueous chromic acid (8M, 1.2 ml and 0.4ml) at intervals. Aqueous sodium metabisulphite was then added to terminate the reaction and the mixture concentrated in vacuo. The concentrate was diluted with water and extracted twice with ethyl acetate. The combined extracts was washed with water and brine, dried over magnesium sulphate, filtered and evaporated to a foam. 2-(4-Acetamidobenzenesulphonyl)-3-carboxy-3,6-dihydro-6-(4-ethoxyphenyl)-5-methyl-2H-1,2-oxazine crystallised as a white power from chloroform. 1H NMR (CDCl3)δ 1.40(3H, t) 1.48(3H, s), 2.15(2H, s), 4.01(2H, q), 4.97(1H, d), 5.29(1H, s), 5.85(1H, d), 6.75(2H, d), 7.19(2H, d), 7.68(2H, d), 7.22(2H, d).

Workup

  1. customto terminate
  2. customthe reaction
  3. concentrationthe mixture concentrated in vacuo
  4. additionThe concentrate was diluted with water
  5. extractionextracted twice with ethyl acetate
  6. washThe combined extracts was washed with water and brine
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated to a foam
  10. custom2-(4-Acetamidobenzenesulphonyl)-3-carboxy-3,6-dihydro-6-(4-ethoxyphenyl)-5-methyl-2H-1,2-oxazine crystallised as a white power from chloroform

Sources & evidence

ORD record
ord-68ad28dee66f48afb5caea2144f55e87
Source dataset
uspto-grants-2002_11
Patent number
US06482824B1

Linked notes

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