Ethanol → 3-{3-Benzyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-2-ethoxy-propionic acid

HRID 1628186Notes

Reaction equation

HRID 1628186 reaction equation
C([O:8][C:9](=[O:44])[CH:10]([O:41][CH2:42][CH3:43])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19](=[O:33])[CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:24][C:25]=2[CH3:26])=[C:14]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:13]=1)C1C=CC=CC=1.CCO>CCOC(C)=O>[CH2:34]([C:14]1[CH:13]=[C:12]([CH2:11][CH:10]([O:41][CH2:42][CH3:43])[C:9]([OH:44])=[O:8])[CH:17]=[CH:16][C:15]=1[O:18][C:19](=[O:33])[CH2:20][C:21]1[N:22]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:24][C:25]=1[CH3:26])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 668644523-{3-Benzyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-2-ethoxy-propionic acid benzyl ester

Product 1

HCID 581194603-{3-Benzyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-2-ethoxy-propionic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared from 3-{3-benzyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-2-ethoxy-propionic acid benzyl ester (0.054 g, 0.09 mmol) in the same manner as described for example 1 with the difference that EtOH was used as the solvent instead of EtOAc. The crude product was purified by column chromatography using DCM/MeOH (95:5) as the eluent and the desired compound was obtained as an oil (0.019 g, 41.3%). 1H NMR (400 MHz, CDCl3): δ 7.93-7.96 (m, 2H), 7.39-7.41 (m, 3H), 7.02-7.19 (m, 8H), 3.99 (m, 1H), 3.86 (s, 2H), 3.69 (s, 2H), 3.48 (m, 1H), 3.32 (m, 1H), 3.03-3.09 (dd, 1H), 2.90-2.93 (dd, 1H), 2.29 (s, 3H), 1.04-1.07 (t, 3H).

Workup

  1. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-1acb395ee4214840aea18e141c1d5088
Source dataset
uspto-grants-2014_07
Patent number
US08785681B2

Reaction notes

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