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Methanesulfonic Acid → 5-Hydroxy-3-oxo-1-phenylindane-2-carboxylate isopropyl amide

HRID 17885
ノート
印刷プレビュー

反応式

HRID 17885 の反応式
C([O:8][C:9]1[CH:10]=[C:11]([CH:28]=[CH:29][CH:30]=1)[C:12]([C:14](=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])=[O:13])C1C=CC=CC=1.CS(O)(=O)=[O:33].C(=O)(O)[O-].[Na+]>ClCCl>[CH:18]([NH-:17])([CH3:20])[CH3:19].[OH:8][C:9]1[CH:10]=[C:11]2[C:28](=[CH:29][CH:30]=1)[CH:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH:14]([C:15]([O-:33])=[O:16])[C:12]2=[O:13]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 866140272-(3-benzyloxybenzoyl)-N-isopropyl-3-phenylacryl amide

生成物 1

HCID 866140285-Hydroxy-3-oxo-1-phenylindane-2-carboxylate isopropyl amide収率 4,150.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(3-Benzyloxybenzoyl)-N-isopropyl-3-phenylacryl amide (106.74 g, 267.19 mmol) was dissolved in dichloromethane. Methanesulfonic acid (256.78 g, 2.672 mmol) was added thereto and the mixture was stirred for 3 hours at room temperature. After the reaction was completed, the mixture was cooled to 0° C. followed by adding saturated sodium bicarbonate, and the organic layer extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography (ethyl acetate:hexane=1:2) to obtain 5-hydroxy-3-oxo-1-phenylindane-2-carboxylate isopropyl amide (36.086 g, yield 44%) as a white solid.

後処理

  1. temperaturethe mixture was cooled to 0° C.
  2. extractionthe organic layer extracted with dichloromethane
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customthe resulting residue was purified by column chromatography (ethyl acetate:hexane=1:2)

出典と根拠

ORDレコード
ord-2e8c6c92f3e64e2ba716f5a6f60730ef
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07741323B2

反応ノート

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