Absolute Configuration of (R)-1-Phenylethylammonium (S)-2-(6-Methoxy-2-naphthyl)propionate

On the influence of using a zwitterionic coformer for cocrystallization: structural focus on naproxen–proline cocrystals

“…The heating rate was 5 uC min 21 over a range from 25 to 300 uC. All experiments were performed under nitrogen atmosphere (rate flow of 50 ml min 21 ).…”

“…13 Four polymorphs of (S)-naproxen have been claimed, but three of them have been obtained under extreme crystallization conditions. Four naproxen cocrystals [14][15][16][17] and eight salts [18][19][20][21][22][23][24][25] have been recorded in the Cambridge Structural Database (CSD), 26 underlining the interest for this compound in solid-state studies. To diversify the structural study, we considered all possible chiral combinations between both partners as shown in Table 1.…”

Ethyl (6-bromo-2-naphthyloxy)acetate

“…For related literature, see: Bachechi et al (1997); Dupont et al (1996); Ravikumar et al (1985); Sarojini et al (2007); Sharma et al (2004); Yathirajan et al (2007); Ye et al (2006).…”

“…Naproxen is a member of the 2arylpropionic acid (profen) family of NSAIDs. The structures the related compounds viz., naproxen (Ravikumar et al, 1985), 6-methoxy-2-naphthyl acetic acid ester-glycolamide (Sharma et al, 2004), 1-(5-chloro-6-methoxynaphthalen-2yl)propan-1-one (Ye et al, 2006), complex of a lisuride derivative and (S)-naproxen (Bachechi et al, 1997), absolute configuration of (R)-1-phenylethylammonium (S)-2-(6-methoxy-2-naphthyl)propionate (Dupont et al, 1996), N′-isopropylidene-6-methoxy-2-naphthohydrazide (Sarojini et al, 2007), ethyl 6-methoxy-2-naphthoate (Yathirajan et al, 2007) have been published. A new derivative was prepared and its crystal structure is reported.…”

Design and synthesis of solid state structures with conjugate acid–base pair interactions

“…To illustrate the potential of designing new solid state structures using CABP hydrogen bonding interactions, we have chosen Naproxen (NAP), a monocarboxylic acid containing API, and Nicotinamide (NICA), a vitamin B containing monobasic (pyridyl) functionality as our model compounds (Scheme 1). Despite the fact that both molecules have been extensively studied in the past, [35][36][37][38][39][40][41][42][43][44][45][46] solid state structures containing the CABP interactions have not been reported. Furthermore, since sodium salts and hydrochloride salts are the most pharmaceutically acceptable 47,48 we chose to synthesize hydrochloride and sodium salts of NAP and NICA, respectively, using the CABP interactions (see supporting information,{ S1).…”