Methanesulfonic Acid → HCID 68783011, compound

HRID 2266520Notes

Reaction equation

HRID 2266520 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([NH2:13])[CH:7]=1.C([O:17][C:18](=O)[CH:19]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)[C:20](=O)[CH2:21][CH3:22])C.CS(O)(=O)=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]2[C:7]=1[C:18](=[O:17])[C:19]([CH2:24][C:25]1[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=1)=[C:20]([CH2:21][CH3:22])[NH:13]2

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 66717604Methyl 2-(3-amino-4-chlorophenoxy)acetateHCID 66717606HCID 66717606, compound

Product 1

HCID 68783011HCID 68783011, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of (3-amino-4-chlorophenoxy)acetic acid methyl ester (0.53 g), 2-(4-chlorobenzyl)-3-oxopentanoic acid ethyl ester (0.66 g), methanesulfonic acid (0.032 mL) and toluene (20 mL) was heated at reflux for 20 hours. The mixture was cooled to room temperature and the solvent removed under reduced pressure. The residue was diluted with water, extracted with ethyl acetate and the combined extracts dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (9:1 by volume) to afford title compound, 0.034 g

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hours
  3. customthe solvent removed under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. dry with materialthe combined extracts dried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue purified by column chromatography on silica gel
  9. washeluting with a mixture of dichloromethane and ethyl acetate (9:1 by volume)

Sources & evidence

ORD record
ord-7474ca0ee84c49a2a921ba068c56cba6
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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