5-(2-Pyridyl)oxazole → 1-Oxo-1-[5-(2-pyridyl)oxazol-2-yl]-3-(4-benzylphenyl)propane

HRID 386440Notes

Reaction equation

HRID 386440 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[O:11][CH:10]=[N:9][CH:8]=1.[CH2:12]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27](O)=[O:28])=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[O:28]=[C:27]([C:10]1[O:11][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:8][N:9]=1)[CH2:26][CH2:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 7371945-(2-Pyridyl)oxazoleHCID 206529113-(4-Benzylphenyl)propanoic acid

Product 1

HCID 167351621-Oxo-1-[5-(2-pyridyl)oxazol-2-yl]-3-(4-benzylphenyl)propaneYield 59%

Procedure

This material was prepared from 5-(2-pyridyl)oxazole and 3-(4-benzylphenyl)propanoic acid (S40) using General Procedure B. PTLC (SiO2, 50% EtOAc-hexanes) afforded 11h (95 mg, 0.59 mmol, 59%) as a light tan oil: 1H NMR (CDCl3, 500 MHz) 8.68 (app d, 1H, J=4.8 Hz), 7.88 (s, 1H), 7.84 (d, 1H, J=7.7 Hz), 7.81 (td, 1H, J=7.7, 1.8 Hz), 7.33-7.27 (m, 3H), 7.21-7.12 (m, 7H), 3.96 (s, 2H), 3.45 (t, 2H, J=7.7 Hz), 3.09 (t, 2H, J=7.7 Hz); 13C NMR (CDCl3, 125 MHz) 187.3, 157.1, 153.2, 150.0, 146.1, 141.1, 139.0, 138.0, 137.0, 129.0, 128.8, 128.5, 128.3, 126.9, 125.9, 124.1, 120.3, 41.4, 40.6, 29.2; IR (film) νmax 3025, 2920, 1694, 1601, 1574, 1516, 1494, 1468, 1426, 1381, 1283, 1151, 1118, 1064, 990, 963, 936, 913, 849, 784, 727, 696 cm−1; ESI-TOF m/z 369.1600 (C24H20N2O2+H+ requires 369.1597).

Sources & evidence

ORD record
ord-068b95b7d85047f08a3f95dcaa6fb167
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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