Methyl 2-(2-(7-phenylheptanoyl)oxazol-5-yl)isonicotinate → 2-(2-(7-Phenylheptanoyl)oxazol-5-yl)isonicotinic acid

HRID 605648Notes

Reaction equation

HRID 605648 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[O:16][C:17]([C:20]3[CH:21]=[C:22]([CH:27]=[CH:28][N:29]=3)[C:23]([O:25]C)=[O:24])=[CH:18][N:19]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CC(O)=O.CCOC(C)=O>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[O:16][C:17]([C:20]3[CH:21]=[C:22]([CH:27]=[CH:28][N:29]=3)[C:23]([OH:25])=[O:24])=[CH:18][N:19]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 16110655Methyl 2-(2-(7-phenylheptanoyl)oxazol-5-yl)isonicotinate

Product 1

HCID 161107142-(2-(7-Phenylheptanoyl)oxazol-5-yl)isonicotinic acidYield 21.1%

Reagents, catalysts & solvents 1

HCID 22609514Ethyl acetate acetateSolvent

Procedure

The title compound was prepared from methyl 2-(2-(7-phenylheptanoyl)oxazol-5-yl)isonicotinate (12 mg, 0.025 mmol) following General Procedure E. Preparative thin layer chromatography (2% AcOH/EtOAc) yielded the title compound as a white solid (2 mg, 17%): 1H NMR (CDCl3, 600 MHz) 8.85 (d, 1H, J=4.2 Hz), 8.42 (s, 1H), 7.93-7.90 (m, 2H), 7.26-7.30 (m, 2H), 7.17-7.16 (m, 3H), 3.12 (t, 2H, J=7.5 Hz), 2.61 (t, 2H, J=7.6 Hz), 1.79 (quint, 2H, J=7.4 Hz), 1.65 (quint, 2H, J=7.5 Hz), 1.44-1.40 (m, 4H); MALDI-FTMS m/z 377.1523 (M−H−, C22H21N2O4, requires 377.1507).

Sources & evidence

ORD record
ord-b0d7372d2d9f44cab0b4861822786e00
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

Loading…