- Resolution of (RS)-Binol through co-crystal formation with 3-n-propyl-4-((R/S)-1′-phenylethylamino)butanoic acid
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A method for the optical resolution of (RS)-Binol to obtain optically pure (S)-Binol (99% ee) through co-crystal formation with (RS)-3-n-propyl-4-((S)- 1′-phenylethylamino)butanoic acid (3RS, 1′S) and similarly optically pure (R)-Binol (99% ee) through co-crystal formation with (RS)-3-n-propyl-4- ((R)-1′-phenylethylamino)butanoic acid (3RS,1′R), in high yield is reported. The individual co-crystal of optically pure (S)-3-n-propyl-4-((S)- 1′-phenylethylamino)butanoic acid (3S,1′S) (99% ee) with (S)-Binol, and (R)-3-n-propyl-4-((S)-1′-phenylethylamino)butanoic acid (3R,1′S) (90% ee) with (S)-Binol have been analyzed by single crystal X-ray diffraction to understand hydrogen bonding in the crystal structure and the chiral recognition parameters.
- Roy, Bhairab Nath,Singh, Girij Pal,Lathi, Piyush Suresh,Mitra, Rangan,Nath, Naba K.,Kalyanachakravarthi,Nangia, Ashwini
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p. 394 - 404
(2013/05/08)
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- THREE COMPONENT CO-CRYSTAL FORMATION BETWEEN DIASTEREOMERIC MIXTURES OF 3-ALKYL-4-((S)-1'PHENYLETHYLAMINO) BUTANOIC ACID AND OPTICALLY PURE 1, 1'-BI-2-NAPHTHOL
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A ternary co-crystal consisting of 1 :0.5:0.5 molar proportion of (S)-1,1'-bi-2-naphthol, 3(S)-propyl-4-[(S)1 '-phenyl-ethylamino]-butanoic acid and 3(R)-propyl-4-[(S)1'- phenyl-ethylamino]-butanoic acid having characteristic powder X-ray diffraction pattern with 2Θ values of 8.41, 9.38, 10.32, 12.16, 15.52, 15.51, 17.84, 17.95, 19.16, 20.37, 21.74, 22.55, 24.44, 25.65, 28.40, 29.15, 29.69, 31.31, 33.54, 34.40, 35.43 (±0.2) and having differential scanning calorimetric peak at about 189.23 ° C when analyzed at the rate of heating of 10°C per minute and process for preparing the same. A process for resolution of (S)-1,1'-bi-2-naphthol from RS-1,1'-bi-2-naphthol.
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Page/Page column 28
(2012/02/02)
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