Chloroform → 7-{2-[4-(4-Fluorophenoxy)-3-hydroxybutyl]-1,1,4-trioxo-3-thiazolidinyl}heptanoic Acid
反応式
C([O:8][CH:9]([CH2:36][O:37][C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=1)[CH2:10][CH2:11][CH:12]1[N:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]CC2C=CC=CC=2)=[O:24])[C:15](=[O:33])[CH2:14][S:13]1(=[O:35])=[O:34])C1C=CC=CC=1.C(Cl)(Cl)Cl>C(O)C.C(OCC)(=O)C>[F:44][C:41]1[CH:40]=[CH:39][C:38]([O:37][CH2:36][CH:9]([OH:8])[CH2:10][CH2:11][CH:12]2[N:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:15](=[O:33])[CH2:14][S:13]2(=[O:34])=[O:35])=[CH:43][CH:42]=1参加物
4
実験手順
A solution of benzyl 7-{2-[3-benzyloxy-4-(4-fluorophenoxy)butyl]-1,1,4-trioxo-3-thiazolidinyl}heptanoate (1.1 g., 1.76 millimole) in absolute ethanol-ethyl acetate (100:2; v:v; 102 ml.) is magnetically stirred and hydrogenated at 25° C. and atmospheric pressure in the presence of 10% palladium/charcoal until hydrogen consumption ceases (~139 ml. of hydrogen is consumed). After removing the catalyst by filtration, the filtrate is concentrated in vacuo leaving an oily residue which is applied to a silica gel column (20 g.) with chloroform. Impurities are eluted with chloroform-acetic acid (25:1; v:v; 200 ml.); continued elution with the same eluant (375 ml.) affords the title compound as a tlc homogeneous, viscous oil (0.59 g., 75%); pmr (CDCl3) δ2.31 (2H, t), 2.73-3.37 (H, m), 3.60-4.30 (6H, m, containing singlets at 3.80 and 3.90), 4.61 (H, t), 6.67-7.60 (6H, m, containing a broad singlet at 7.30).