5-Methyl-2-phenyl-4-oxazoleacetic acid → HCID 66865470, compound

HRID 709477Notes

Reaction equation

HRID 709477 reaction equation
C(OC(=O)C(OCC)CC1C=CC(O)=C(C)C=1)C1C=CC=CC=1.CC1OC(C2C=CC=CC=2)=NC=1CC(O)=O.[CH2:40]([O:47][C:48](=[O:83])[CH:49]([O:80][CH2:81][CH3:82])[CH2:50][C:51]1[CH:56]=[CH:55][C:54]([O:57][C:58](=[O:72])[CH2:59][C:60]2[N:61]=[C:62]([C:66]3[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=3)[O:63][C:64]=2[CH3:65])=[C:53]([CH2:73]C2C=CC=CC=2)[CH:52]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>>[CH2:40]([O:47][C:48](=[O:83])[CH:49]([O:80][CH2:81][CH3:82])[CH2:50][C:51]1[CH:56]=[CH:55][C:54]([O:57][C:58](=[O:72])[CH2:59][C:60]2[N:61]=[C:62]([C:66]3[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=3)[O:63][C:64]=2[CH3:65])=[C:53]([CH3:73])[CH:52]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

4

Reactant 3

HCID 27751395-Methyl-2-phenyl-4-oxazoleacetic acidHCID 668644523-{3-Benzyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-2-ethoxy-propionic acid benzyl esterHCID 668649262-Ethoxy-3-(4-hydroxy-3-methyl-phenyl)-propionic acid benzyl ester

Product 1

HCID 66865470HCID 66865470, compound

Procedure

The title compound was prepared from 2-ethoxy-3-(4-hydroxy-3-methyl-phenyl)-propionic acid benzyl ester (311 mg, 0.98 mmol) and (5-methyl-2-phenyl-oxazol-4-yl)-acetic acid (215 mg, 0.98 mmol) in the same manner as described for 3-{3-benzyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-2-ethoxy-propionic acid benzyl ester. The crude product was purified by column chromatography using DCM/iPrOH (95:5) as the eluent to afford the pure product as a solid (480 mg, 94.5%). 1H NMR (400 MHz, CDCl3): δ 7.98-8.02 (m, 2H), 7.26-7.44 (m, 8H), 6.91-7.05 (m, 3H), 5.12 (s, 2H), 4.01-4.05 (t, 1H), 3.82 (s, 2H), 3.56-3.59 (m, 1H), 3.34-3.37 (m, 1H), 2.95-2.97 (d, 2H), 2.43 (s, 3H), 2.11 (s, 3H), 1.12-1.17 (t, 3H).

Workup

  1. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-2c50675b1bcd41ac8647474fb6c663b0
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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