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

HRID 324084Notes

Reaction equation

HRID 324084 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:35])[C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[C:25]([Cl:30])[CH:24]=3)[C:20]([O:31][CH2:32][CH2:33][OH:34])=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N+]1([O-])CC[O:40]CC1.O.CC#N>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O.CCOC(C)=O>[Cl:30][C:25]1[CH:24]=[C:23]([C:21]2[CH:22]=[C:17]([C:16](=[O:35])[NH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:18]=[CH:19][C:20]=2[O:31][CH2:32][C:33]([OH:40])=[O:34])[CH:28]=[CH:27][C:26]=1[F:29]

Participants

8

Reactant 4

HCID 962Water2×HCID 6342AcetonitrileHCID 82029Methyl morpholine oxide2×HCID 22237531N-(8-Phenyloctyl)4-(2-hydroxyethoxy)-5-(3-chloro-4-fluorophenyl)benzamide

Product 1

HCID 22237602[3'-Chloro-4'-fluoro-5-(8-phenyl-octylcarbamoyl)-biphenyl-2-yloxy]acetic acidYield 34%

Reagents, catalysts & solvents 3

HCID 178419074HCID 178419074, compoundCatalyst2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  1. stirringthe reaction was stirred overnight

Sources & evidence

ORD record
ord-0ffabce258a842fcbfced0f99bd9bf84
Source dataset
uspto-grants-2001_04
Patent number
US06214877B1

Reaction notes

Loading…