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

HRID 17885
Notes
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Reaction equation

HRID 17885 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-2e8c6c92f3e64e2ba716f5a6f60730ef
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07741323B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes