methyl (2E)-3-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]vinyl}thiophen-2-yl)acrylate → Methyl 3-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}thiophen-2-yl)propionate

HRID 1892508Notes

Reaction equation

HRID 1892508 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](/[CH:17]=[CH:18]/[C:19]([O:21][CH3:22])=[O:20])[S:15][CH:16]=2)[N:9]=1)(=[O:3])[CH3:2]>C(OCC)(=O)C.C(O)(=O)C.[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]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[S:15][CH:16]=2)[N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 1

HCID 86650010methyl (2E)-3-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]vinyl}thiophen-2-yl)acrylate

Product 1

HCID 86650011Methyl 3-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}thiophen-2-yl)propionateYield 83%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl (2E)-3-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]vinyl}thiophen-2-yl)acrylate (3.000 g, 8.971 mmol) was dissolved in ethyl acetate (400 ml) and acetic acid (100 ml). 20% Palladium carbon was added, and the mixture was hydrogenated at room temperature under an atmospheric pressure. After the completion of the reaction, the catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP, 100 g, ethyl acetate:hexane=2:3) to give methyl 3-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}thiophen-2-yl)propionate (2.521 g, 7.449 mmol, yield 83.0%) as a pale-yellow solid.

Workup

  1. customwas hydrogenated at room temperature under an atmospheric pressure
  2. customAfter the completion of the reaction
  3. filtrationthe catalyst was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP, 100 g, ethyl acetate:hexane=2:3)

Sources & evidence

ORD record
ord-3678270f6118416f93851d70e6468f9d
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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