Methanol → HCID 53703941, compound

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([S:16]([CH2:18][C:19]([OH:21])=[O:20])=[O:17])[CH3:15])=[CH:10][CH:9]=1.CO.[CH:24]1(N=C=NC2CCCCC2)CCCCC1>C1C=CC=CC=1>[CH3:24][O:20][C:19](=[O:21])[CH2:18][S:16]([CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[CH:9][CH:10]=1)[CH3:15])=[O:17]

Participants

Procedure

800 gm (2.61 mol) of the difficultly soluble diastereoisomer of [1-(2'-fluoro-4-biphenylyl)-ethylsulfinyl]-acetic acid, m.p. 164°-165° C., were suspended in 4 liters of benzene and 125.5 gm (3.92 mol) of methanol, and a solution of 648 gm (3.14 mol) of dicyclohexyl-carbodiimide in 650 ml of benzene was added while stirring and cooling at 20°-25° C. The acid dissolved, and dicyclohexylurea precipitated out. The mixture was allowed to stand overnight at room temperature, then the excess of carbodiimide was decomposed by addition of glacial acetic acid, and then 2 liters of water were added, the dicyclohexylurea was suction-filtered off, the organic phase was separated from the filtrate and evaporated in vacuo after drying. The obtained oil (969 gm) was recrystallized from 2.9 liters of isopropanol. Yield: 736 gm (88% of theory); m.p. 75°-77° C.