content_image/942355.jpg
# United States Patent c19J 

# Felder et al. 

# [54] PROCESS FOR THE RESOLUTION OF ( + )• AND $_{(-}$)~6-METHOXY-a-METHYL-2-NAPH› THALENEACETIC ACID 

[75] Inventors: Ernst Felder, Riva San Vitale, Switzerland; Davide Pitre, Milan, Italy; Hans $_{Zutter, }$Schaftbausen, Switzerland 

[73] Assignee: Syntex Corporation, Panama 

[21] Appl. No.: 55,427 

[22] Filed: Jul. 6, 1979 

## [30] Foreign Application Priority Data 

Jul. 19, 1978 [CH] Switzerland ......................... 7777/78 

[51] Int. 0.3 ...................... C07C 91/10; C07C 65/24; C07B 19/00 

[52] U.S. a ................................ 260/501.17; 562/466; 562/401; 564/507 

[58] Field of Search ...................... 260/501.17, 584 R; 562/466, 401 

## [56] References Cited 

2,016,962 10/1935 Flint et al. ....................... 260/584 R 

## U.S. PATENT DOCUMENTS 

<img src='content_image/942355.jpg'>

Greenstein et al., Chem. of the Amino Acids, John Wiley & Sons, Inc., N.Y. vol. 1, pp. 715-728 (1961). 

Primary Examiner-Joseph E. Evans 

Assistant Examiner-G. T. Breitenstein 

Attorney, Agent, or Firm-Joseph I. Hirsch; John A. Dhuey 

## [57] ABSTRACT 

The subject of the invention is a process for resolving mixtures of ( + )- and ( - )-6-methoxy-a-methyl-2-naph› thaleneacetic acid into the enantiomers thereof, charac› terized in that N-methyl-D-glucamine [= 1-deoxy-1- (methylamino)-D-glucitol] is used as the resolving agent, so that $_{the }$6-methoxy-a-methyl-2-naphthalenea› cetic acid is converted into the corresponding diastereo› isomeric N-methyl-D-glucamine salt pair which, be› cause of very different solubilities, can be separated easily and completely with high yield. 

## OTHER PUBLICATIONS 

## 19 Claims, No Drawings 

# [11] 4,246,164 

# [45] Jan. 20, 1981 

