HCID 86650004, compound → HCID 86650003, compound

HRID 1892498Notes

Reaction equation

HRID 1892498 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH:10]=[CH:11][C:12]2[CH:13]=[C:14]([CH2:18][C:19]([OH:21])=[O:20])[CH:15]=[CH:16][CH:17]=2)[N:9]=1)(=[O:3])[CH3:2]>O1CCCC1.CO.[C].[Pd]>[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][CH2:11][C:12]2[CH:13]=[C:14]([CH2:18][C:19]([OH:21])=[O:20])[CH:15]=[CH:16][CH:17]=2)[N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 1

HCID 86650004HCID 86650004, compound

Product 1

HCID 86650003HCID 86650003, compoundYield 91.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-{2-[2-(Acetylamino)-1,3-thiazol-4-yl]vinyl}phenylacetic acid (4.500 g, 14.88 mmol) was dissolved in a mixed solvent of tetrahydrofuran (225 ml) and methanol (90 ml), and 20% palladium carbon (containing 50% water, 1.800 g) was added. Hydrogenation was performed at room temperature −30° C., 4 atm. After the completion of the reaction, the reaction mixture was filtered through celite, and the filtrate was concentrated. Diethyl ether (100 ml) was added to the residue, and the precipitate was collected by filtration. The filtered product was washed 3 times with diethyl ether, and dried under reduced pressure to give 3-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}phenylacetic acid (4.152 g, 13.64 mmol, yield 91.7%) as a white solid.

Workup

  1. additionwas added
  2. customwas performed at room temperature −30° C.
  3. customAfter the completion of the reaction
  4. filtrationthe reaction mixture was filtered through celite
  5. concentrationthe filtrate was concentrated
  6. additionDiethyl ether (100 ml) was added to the residue
  7. filtrationthe precipitate was collected by filtration
  8. washThe filtered product was washed 3 times with diethyl ether
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-77d10062c25e4a7b9cc5f8364616a6a5
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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