Methanesulfonic Acid → HCID 23157372, compound

HRID 508060Notes

Reaction equation

HRID 508060 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([O:23]COC)=[CH:18][C:17]=3[CH3:27])[CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[CH2:28][CH2:29][C:30]([OH:32])=[O:31].CS(O)(=O)=O>C(OCC)(=O)C.C(OCC)C>[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]3[C:17]([CH3:27])=[CH:18][C:19]([OH:23])=[CH:20][C:21]=3[CH3:22])[CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[CH2:28][CH2:29][C:30]([OH:32])=[O:31]

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 23157310HCID 23157310, compound

Product 1

HCID 23157372HCID 23157372, compoundYield 9.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-[2-Fluoro-4-({[4′-(methoxymethoxy)-2′,6′-dimethylbiphenyl-3-yl]methyl}amino)phenyl]propanoic acid (1.0 g, 2.29 mmol) was dissolved in ethyl acetate (2 mL) and diethyl ether (4 mL). To this solution was added methanesulfonic acid (0.16 mL, 2.47 mmol) and the solution was concentrated under reduced pressure. Aqueous sodium hydrogencarbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate, concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (85 mg, yield 9%) as a colorless oil.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. additionAqueous sodium hydrogencarbonate solution was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-e01c5920b6974f82a216454cc798ec75
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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