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

HRID 1018480노트

반응식

HRID 1018480 반응식
[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]

참가 물질

5

반응물 3

HCID 24425Chromic Acid2회HCID 656671Sodium PyrosulfiteHCID 184015412-(4-acetamidobenzenesulphonyl)-3,6-dihydro-6-(4-ethoxyphenyl)-3-hydroxymethyl-5-methyl-2H-1,2-oxazine

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-68ad28dee66f48afb5caea2144f55e87
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06482824B1

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