4-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-benzoic acid methyl ester → HCID 58930546, compound

HRID 416287Notes

Reaction equation

HRID 416287 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]2[S:15][C:14](=[O:16])[NH:13][C:12]2=[O:17])=[CH:6][CH:5]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH:11]2[S:15][C:14](=[O:16])[NH:13][C:12]2=[O:17])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 6060034-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-benzoic acid methyl ester

Product 1

HCID 58930546HCID 58930546, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A solution of the methyl ester 350 (615 mg, 2.32 mmol) in MeOH (120 ml) was hydrogenated over 10% Pd/C (615 mg, Degussa type) for 2 hours at room temperature. Another portion of Pd/C (300 mg) was added and the hydrogenation proceeded for another 3 hrs (monitored by MS). The reaction mixture was filtered through a celite pad, evaporated and the residue was purified by flash chromatography, eluent EtOAc—CH2Cl2 (1:2), to produce the title compound (570 mg, 92% yield). LRMS: 265.3 (calcd.), 266.1 [MH]+ (found).

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. customevaporated
  3. customthe residue was purified by flash chromatography, eluent EtOAc—CH2Cl2 (1:2)

Sources & evidence

ORD record
ord-d0b71bd2fea94fddbb14de0690abc7b6
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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