2-Thiazoleacrylic acid → 3-(2-Thiazolyl)propionic acid

HRID 915663Notes

Reaction equation

HRID 915663 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[CH:7][C:8]([OH:10])=[O:9]>C(O)C.[Pd]>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

4

Reactant 1

HCID 534018492-Thiazoleacrylic acid

Product 1

HCID 27606093-(2-Thiazolyl)propionic acidYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Mix and suspend 3-thiazol-2-yl-acrylic acid (580 mg, 3.74 mmol) and 5% Pd/C (270 mg) in ethanol (200 mL). Purge the mixture with nitrogen. Then purge with hydrogen for 30 minutes and stir under 1 atmosphere of hydrogen for 6 hours. Filter the reaction mixture through Celite® and wash the filter cake with additional ethanol. Concentrate the filtrate to afford 550 mg (94%) of 3-thiazol-2-yl-propionic acid as a white solid. MS: m/e=158 (MH+).

Workup

  1. additionMix
  2. customPurge the mixture with nitrogen
  3. customThen purge with hydrogen for 30 minutes
  4. filtrationFilter the reaction mixture through Celite®
  5. washwash the filter cake with additional ethanol
  6. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-c4b0121387b140dcbd9640dfe737554d
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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