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

HRID 1018480

反応式

HRID 1018480 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-68ad28dee66f48afb5caea2144f55e87
出典データセット
uspto-grants-2002_11
特許番号
US06482824B1

関連ノート

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