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

HRID 709500Notes

Reaction equation

HRID 709500 reaction equation
C([O:8][C:9](=[O:37])[C@@H:10]([O:34][CH2:35][CH3:36])[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])=[CH:14][CH:13]=1)C1C=CC=CC=1.[H][H]>CCOC(C)=O.[Pd]>[CH2:35]([O:34][C@@H:10]([CH2:11][C:12]1[CH:13]=[CH:14][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])=[CH:16][CH:17]=1)[C:9]([OH:37])=[O:8])[CH3:36]

Participants

5

Reactant 2

HCID 66864611(S)-2-Ethoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-propionic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 58119473(S)-2-Ethoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-propionic acidYield 96.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(S)-2-Ethoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-propionic acid benzyl ester (0.1 g, 0.2 mmol) was dissolved in EtOAc (4 mL) and 10% Pd/C (0.04 g, 0.037 mmol) was added. After evacuation the reaction vessel was connected to a hydrogen line and the hydrogenation was performed at atmospheric pressure at room temperature for 3 h. The catalyst was filtered off, washed with EtOAc and the combined organic filtrates were evaporated under reduced pressure to afford the product as a solid (0.079 g, 96.4%). 1H NMR (400 MHz, CDCl3): δ 7.98-7.99 (d, 2H), 7.42 (m, 3H), 7.23-7.25 (d, 2H), 7.02-7.04 (m, 2H), 6.71 (br s, 1H), 4.01-4.02 (m, 1H), 3.80 (s, 2H), 3.57-3.60 (m, 1H), 3.36-3.39 (m, 1H), 3.07-3.10 (m, 1H), 2.94-2.99 (m, 1H), 2.40 (s, 3H), 1.11-1.14 (t, 3H).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with EtOAc
  3. customthe combined organic filtrates were evaporated under reduced pressure

Sources & evidence

ORD record
ord-ac4a22e5e54d47aca7eaa8611082c225
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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