NO126859B

1291386 Salts and resolved optical isomers of 2 - (61 - substituted - 21- naphthyl) propionic acids SYNTEX CORP 20 Jan 1970 [24 March 1969] 2764/70 Addition to 1211134 Heading C2C Novel compounds of the Formula I wherein one of R1 and R2 is hydrogen and the other is methyl or difluoromethyl; R3 is methyl, ethyl, isopropyl, cyclopropyl, trifluoromethyl, vinyl, ethynyl, fluoro, chloro, methoxy, methoxymethyloxy, difluoromethoxy, methyl thio, methoxymethyl thio or difluoromethyl thio, either in the form of a mixture of d- and lisomers or resolved isomers of the salts with magnesium, ammonium, R 3 N, ethanolamine, methyl glucamine or ethylenediamine, where R is C 1-6 alkyl except ethyl, monocyclic aralkyl or monocyclic aryl or in the form of the resolved d- and l-forms of the free acid or additionally the sodium, potassium, calcium, aluminium, 2-(diethylamino)ethanol, 2 - (dimethylamino)- ethanol, argurine, lysine, caffeine, procaine and triethylamine salts with the proviso in the latter case that when the compound is in the form of the free acid and the other of R1 and R2 is methyl, R3 is cyclopropyl, vinyl, ethynyl, methoxymethyloxy or methoxylmethyl thio may be prepared by either or both of the steps (a) resolving a compound of the Formula I to obtain a d- or l-isomer and (b) reacting a compound I with a base to form the corresponding salt; and optionally one or more of the following steps; (c) hydrolysis of an ester of a compound I, (d) decarboxylation of a 2-(61-substituted-21- naphthyl) - 2 difluoromethyl malonic acid, (e) etherification of compound I in which R3 is hydroxy or thiol or (f) dehydrobrominating a 2 - [61 - (1,2 - dibromoethyl) - 21 - naphthyl propionic acid to yield a 2-(61-ethylnyl-21-naphthyl) propionic acid, (g) fluorinating a compound I in which R3 is CH 3 S or CH 3 O to R3=CF 2 HS or CF 2 HO; (h) fluorinating I in which R3 is CH 3 - to CF 3 via the trichloro compound, (i) oxidizing I in which R3 is CH 3 CHOH to CH 3 CO; (j) #- methylating a naphthalene acetic ester. The intermediate 2-(61-methoxy-21-naphthyl) acetic acid may be prepared by Friedel-Crafts acetylation of 2-methoxynaphthalene to form 2 - acetyl - 6 - methoxy naphthalene which is converted by a Willgerodt reaction to the required intermediate. The intermediate diethyl 2-(61-methoxy-21- naphthyl) - 2 - difluoromethylmalonate may be - prepared from 2 - (61 - methoxy - 21- naphthyl) acetic acid by esterification followed by treatment with diethyl carbonate in strong base. The