5-(2-Pyridyl)oxazole → HCID 16735160, compound

HRID 386428Notes

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]([O:19][C:20]1[CH:21]=[C:22]([CH2:26][CH2:27][C:28](O)=[O:29])[CH:23]=[CH:24][CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[O:29]=[C:28]([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)[CH2:27][CH2:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([O:19][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:21]=1

Participants

Reactant 2

HCID 7371945-(2-Pyridyl)oxazole

HCID 219385043-(3-(Benzyloxy)phenyl)propanoic acid

Product 1

HCID 16735160HCID 16735160, compoundYield 18%

Procedure

The title compound was prepared from 5-(2-pyridyl)oxazole and 3-(3-(benzyloxy)phenyl)propanoic acid (Bänteli, R.; Brun, I.; et al. Tetrahedron Lett. 1999, 40, 2109-2112) using General Procedure B. Column chromatography (SiO2, 2.5×6 cm, 10-20% EtOAc-hexanes gradient) followed by PTLC (SiO2, 50% EtOAc-hexanes) afforded 11c (46 mg, 0.12 mmol, 18%) as a yellow solid: 1H NMR (CDCl3, 400 MHz) 8.67 (m, 1H), 7.88 (s, 1H), 7.87-7.85 (m, 1H), 7.81 (td, 1H, J=7.8, 1.8 Hz), 7.45 (d, 2H, J=8.5 Hz), 7.38 (t, 2H, J=7.3 Hz), 7.32 (t, 2H, J=6.8 Hz), 7.22 (t, 2H, J=7.9 Hz), 6.92 (d, 2H, J=2.1 Hz), 6.88 (d, 2H, J=7.6 Hz), 6.83 (dd, 2H, J=7.9, 2.4 Hz), 5.06 (s, 2H), 3.47 (t, 2H, J=7.4 Hz), 3.10 (t, 2H, J=7.4 Hz); 13C NMR (CDCl3, 100 MHz) 187.2, 158.9, 157.2, 153.4, 150.1, 146.2, 142.0, 137.1, 137.0, 129.5, 128.5, 127.9, 127.5, 127.0, 124.2, 121.0, 120.4, 115.1, 112.5, 69.9, 40.5, 29.7; IR (film) νmax 3073, 3032, 2929, 1697, 1601, 1582, 1499, 1468, 1452, 1425, 1380, 1256, 1154, 1027, 784, 737, 695 cm−1; ESI-TOF m/z 385.1549 (C24H20N2O3+H+ requires 385.1547).

Sources & evidence

ORD record: ord-fac716d4999a46b5b81cc5208fbaab24
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372823B2

Reaction notes

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