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

HRID 1846837
ノート
印刷プレビュー

反応式

HRID 1846837 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180
Acetone
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-aaa910c5384e44d2a9c78fafa9f052bb
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08952039B2

反応ノート

読み込み中…

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