[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=O)[CH:2]=1.[OH:17][CH2:18][C@H:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>S(Cl)(Cl)=O.N1C=CC=CC=1.C(Cl)Cl>[OH:17][CH2:18][C@H:19]([NH:26][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][CH:15]=[N:16][C:8]=1[O:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1A solution of 2-(Pyridin-3-yloxy)-nicotinic acid (0.250 grams, 1.2 mmole) in thionyl chloride (10 ml) was heated to reflux. After 1 hour the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was suspended in tetrahydrofuran (10 ml) and added dropwise to a solution of (R)-2-hydroxy-1-phenyl ethylamine (0.160 grams, 1.2 mmole) in pyridine (5 ml) at 0° C. After 30 minutes the mixture was warmed to room temperature, stirred at room temperature for 1 hour and concentrated to remove pyridine. The crude product was purified by chromatography on silica gel eluting with ethyl acetate to give a yellow oil. HRMS 336.1324; α=+63.9° 12.3 mg/ml in methylene chloride. 1H NMR (400 mhz, CDCl3) d 2.76 (bs, 1H), 3.95-4.02 (m, 2H), 5.31-5.36 (m, 1H), 7.16-7.40 (m, 1H), 8.19 (dd, J=2.1 Hz, 4.8 Hz, 1H), 8.48-8.61 (m, 4H).
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