Methanesulfonic Acid → HCID 86614028, compound

HRID 17885Notes

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]

Participants

5

Reactant 3

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

Product 1

HCID 86614028HCID 86614028, compoundYield 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
Patent number
US07741323B2

Reaction notes

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