Methyl 6-(2-(7-phenylheptanoyl)oxazol-5-yl)picolinate → 6-[2-(7-Phenylheptanoyl)-1,3-oxazol-5-yl]pyridine-2-carboxylic acid

HRID 605646Notes

Reaction equation

HRID 605646 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[N:25]=[C:24]([C:26]([O:28]C)=[O:27])[CH:23]=[CH:22][CH:21]=3)=[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[N:25]=[C:24]([C:26]([OH:28])=[O:27])[CH:23]=[CH:22][CH:21]=3)=[CH:18][N:19]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 16110656Methyl 6-(2-(7-phenylheptanoyl)oxazol-5-yl)picolinate

Product 1

HCID 161107156-[2-(7-Phenylheptanoyl)-1,3-oxazol-5-yl]pyridine-2-carboxylic acidYield 57%

Reagents, catalysts & solvents 1

HCID 22609514Ethyl acetate acetateSolvent

Procedure

The title compound was prepared from methyl 6-(2-(7-phenylheptanoyl)oxazol-5-yl)picolinate (9 mg, 0.059 mmol) following General Procedure E. Preparative thin layer chromatography (2% AcOH/EtOAc) yielded the title compound as a white solid (5 mg, 57%): 1H NMR (THF-d8, 500 MHz) δ 8.11-8.04 (m, 4H), 7.22-7.08 (m, 5H), 3.08 (t, 2H, J=7.5 Hz), 2.61 (t, 2H, J=7.5 Hz), 1.76-1.68 (m, 2H), 1.68-1.62 (m, 2H), 1.45-1.41 (m, 4H); 13C NMR (THF-d8, 125 MHz) δ 185.6, 163.1, 156.4, 151.4, 147.6, 144.7, 141.0, 137.1, 126.7, 126.5, 126.1, 123.9, 122.8, 121.1, 37.1, 34.3, 30.0, 27.6, 27.5, 22.2; MALDI-FTMS m/z 379.1645 (M+H+, C22H23N2O4, requires 379.1652).

Sources & evidence

ORD record
ord-7509b9214d054acea8002bb6fe77dea7
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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