Water → [3'-Chloro-4'-fluoro-5-(8-phenyl-octylcarbamoyl)-biphenyl-2-yloxy]acetic acid

Participants

Reaction Steps

To a solution of N-(8-phenyloctyl)-4-(2-hydroxyethoxy)-5-(3-chloro-4-fluorophenyl)benzamide (200 mg, 0.415 mmol) in 5 mL CH2Cl2 was added NMMO.H2O (96 mg, 0.712 mmol) and TPAP (12.5 mg, 0,0356 mmol). The reaction was stirred overnight and 50 mg, 0.14 mmol TPAP, 2 mL CH3CN, and 90 mg, 0.665 mmol NMMO.H2O were added and the reaction was stirred overnight. The reaction was worked up as in Step 3 of Example 135. The crude material was subjected to column chromatography (40% EtOAc:60% Hexanes) on HCOOH pretreated silica gel to yield 70 mg, 34% of the acid as a dark yellow oil. 1H NMR (DMSO-d6) 1.22-1.27 (m. 8H); 1.474-1.551 (m, 4H); 2.53 (t, J=7.47 Hz, t); 3.21 (q, J=6.59 Hz, 2H); 4.82 (s, 1H); 7.08-7.17 (m, 4H); 7.22-7.26 (m, 2H); 7.48 (t, J=8.79 Hz, 1H); 7.60-7.64 (m, 1H); 7.80-7.85 (m, 2H); 8.36 (t, J=5.60 Hz, 1H); IR 3400, 2930, 1730, 1600, 1550, 1470, 1210, 1075, and 700 cm−1; mass spectrum [(−)ESI], m/z 510/512 [M−H]−; Anal. Calcd. for C29H30BrClFNO4: C, 97.99; H, 6.10; N, 2.73; Found: C, 66.89; H, 6.17; N. 2.61.

Provenance & Evidence