N-[3-phenyl-3-(thien-2-yl)-2-propenyl]sarcosine ethyl ester → HCID 22225858, compound

HRID 635912Notes

Reaction equation

HRID 635912 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([CH2:8][CH:9]=[C:10]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[CH3:7])[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([CH2:8][CH2:9][CH:10]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[CH3:7])[CH3:2]

Participants

4

Reactant 1

HCID 54147122N-[3-phenyl-3-(thien-2-yl)-2-propenyl]sarcosine ethyl ester2×

Product 1

HCID 22225858HCID 22225858, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.055 g (0.174 mmol) N-[3-Phenyl-3-(thien-2-yl)-2-propenyl]sarcosine ethyl ester (Compound 41 from Example 6) was hydrogenated over 0.055 g 10% Pd/C in 2 ml of EtOH. The hydrogenation was conducted at 40 psi for 16 hours at room temperature (see Reaction 20, FIG. 2). After filtering off the catalyst the solution was concentrated and the residue was purified by preparative TLC with 1:2 ethyl acetate:hexanes to give 0.012 g (22%) N-[3-phenyl-3-(thien-2-yl)propyl]sarcosine ethyl ester (Compound A42) as a yellow oil.

Workup

  1. custom(see Reaction 20, FIG. 2)
  2. filtrationAfter filtering off the catalyst the solution
  3. concentrationwas concentrated
  4. customthe residue was purified by preparative TLC with 1:2 ethyl acetate

Sources & evidence

ORD record
ord-6b607eb47f724f978b54f276485e80a2
Source dataset
uspto-grants-2001_02
Patent number
US06191165B1

Reaction notes

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