Sodium methanethiolate → {2'-[(Cyclopropanecarbonyl-ethyl-amino)-methyl]-6-methoxy-4'-methylsulfanyl-biphenyl-3-yl}-acetic acid

HRID 563703Notes

Reaction equation

C([O:3][C:4](=[O:30])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17](F)=[CH:16][C:15]=2[CH2:21][N:22]([C:25]([CH:27]2[CH2:29][CH2:28]2)=[O:26])[CH2:23][CH3:24])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)C.[CH3:31][S-:32].[Na+]>CN(C=O)C>[CH:27]1([C:25]([N:22]([CH2:21][C:15]2[CH:16]=[C:17]([S:32][CH3:31])[CH:18]=[CH:19][C:14]=2[C:8]2[C:9]([O:12][CH3:13])=[CH:10][CH:11]=[C:6]([CH2:5][C:4]([OH:3])=[O:30])[CH:7]=2)[CH2:23][CH3:24])=[O:26])[CH2:29][CH2:28]1

Participants

Conditions

Temperature: 85 °C

Procedure

To {2′-[(cyclopropanecarbonyl-ethyl-amino)-methyl]-4′-fluoro-6-methoxy-biphenyl-3-yl}-acetic acid ethyl ester 0.186 g, 0.45 mmol) in DMF (0.5 mL) was added sodium thiomethoxide (0.035 g, 0.50 mmol), and the reaction was stirred at 85° C. for 2 hours. Analytical LCMS indicated that starting material was still present, so additional sodium thiomethoxide (0.070 g, 1.0 mmol) was added, and the reaction was stirred at 85° C. for another 2 hours. Analytical LCMS showed that no starting material remained, and that the ethyl ester had been hydrolyzed, so an aqueous work-up was performed, and the residue was purified by preparative HPLC to give the title compound. M+H is 414.

Workup

stirringthe reaction was stirred at 85° C. for another 2 hours
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-b577b137740b4ec8b7ad83e9686d3a9b
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067445B2

Reaction notes

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