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Water → 6-(benzene sulfonyl amino-methyl)-3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid

HRID 1846837
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HRID 1846837 반응식
[CH2:1]([O:8][C:9]1[C:10](=[O:28])[CH:11]=[C:12]([CH2:17][NH:18]S(C2C=CC=CC=2)(=O)=O)[O:13][C:14]=1[CH:15]=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:29](=[O:33])(=O)([OH:31])N.Cl([O-])=O.[Na+].[OH2:38]>CC(C)=O>[C:2]1([S:29]([CH:17]([NH2:18])[C:12]2[O:13][C:14]([C:15]([OH:16])=[O:38])=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:10](=[O:28])[CH:11]=2)(=[O:33])=[O:31])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 86725694N-(5-benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide

생성물 1

HCID 867256956-(benzene sulfonyl amino-methyl)-3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid수율 87.82%

시약·촉매·용매 1

HCID 180
Acetone
용매

실험 절차

To a stirred solution of N-(5-benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide (11-01) (700.0 mg, 1.75 mmol) in acetone (10 mL) and water (15 mL) were added sulfamic acid (240.45 mg, 2.45 mmol) and sodium chlorite (166.6 mg, 1.84 mmol) and the reaction mixture was allowed to stir for 16 h at room temperature. After completion of the reaction, the solvent and the volatile substances were removed and extracted with dichloromethane. The combined organic layer was washed with saturated ammonium chloride solution, water and then brine, dried over Na2SO4 and concentrated under reduced pressure to get 6-(benzene sulfonyl amino-methyl)-3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid (12-01) (640.0 mg, 87.82%) as a white solid.

후처리

  1. customAfter completion of the reaction
  2. customthe solvent and the volatile substances were removed
  3. extractionextracted with dichloromethane
  4. washThe combined organic layer was washed with saturated ammonium chloride solution, water
  5. dry with materialbrine, dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-aaa910c5384e44d2a9c78fafa9f052bb
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08952039B2

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