Methanol → 2-Ethoxy-3-{3-methyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-propionic acid

HRID 709503Notes

Reaction equation

HRID 709503 reaction equation
C([O:8][C:9](=[O:38])[CH:10]([O:35][CH2:36][CH3:37])[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]([CH3:34])[CH:13]=1)C1C=CC=CC=1.CO>CCOC(C)=O>[CH2:36]([O:35][CH:10]([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]([CH3:34])[CH:13]=1)[C:9]([OH:38])=[O:8])[CH3:37]

Participants

4

Reactant 2

HCID 887MethanolHCID 66865470HCID 66865470, compound

Product 1

HCID 581194642-Ethoxy-3-{3-methyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-propionic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared from 2-ethoxy-3-{3-methyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-propionic acid benzyl ester (0.63 g, 1.22 mmol) in the same manner as described for example 1 with the difference that MeOH was used as the solvent instead of EtOAc. The crude product was purified by column chromatography using DCM/iPrOH (95:5) as the eluent and the title compound was obtained as a solid (0.303 g, 58.3%). 1H NMR (500 MHz, CDCl3): δ 7.99-8.02 (m, 2H), 7.43-7.46 (m, 3H), 7.08-7.11 (m, 2H), 6.96-6.97 (d, 1H), 4.01-4.03 (m, 1H), 3.85 (s, 2H), 3.61 (m, 1H), 3.37 (m, 1H), 3.04-3.07 (dd, 1H), 2.95-2.97 (dd, 1H), 2.43 (s, 3H), 2.13 (s, 3H), 1.12-1.14 (t, 3H).

Workup

  1. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-aeb54ccd799648a9a72b991e9b6aff78
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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