3-(3,5-Dimethoxyphenyl)-2-{4-[4-(2,4-dioxothiazolidin-5-ylidenemethyl)-phenoxy]-phenyl}-propionic acid methyl ester → 3-(3,5-Dimethoxyphenyl)-2-{4-[4-(2,4-dioxothiazolidin-5-ylmethyl)-phenoxy]-phenyl}-propionic acid methyl ester

HRID 2217614Notes

Reaction equation

HRID 2217614 reaction equation
[CH3:1][O:2][C:3](=[O:37])[CH:4]([C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH:29]=[C:30]3[S:34][C:33](=[O:35])[NH:32][C:31]3=[O:36])=[CH:25][CH:24]=2)=[CH:18][CH:17]=1)[CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[CH:7]=1>O1CCOCC1.[Pd]>[CH3:1][O:2][C:3](=[O:37])[CH:4]([C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH:30]3[S:34][C:33](=[O:35])[NH:32][C:31]3=[O:36])=[CH:25][CH:24]=2)=[CH:18][CH:17]=1)[CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[CH:7]=1

Participants

4

Reactant 1

HCID 865896813-(3,5-Dimethoxyphenyl)-2-{4-[4-(2,4-dioxothiazolidin-5-ylidenemethyl)-phenoxy]-phenyl}-propionic acid methyl ester

Product 1

HCID 98713823-(3,5-Dimethoxyphenyl)-2-{4-[4-(2,4-dioxothiazolidin-5-ylmethyl)-phenoxy]-phenyl}-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 312751,4-DioxaneSolvent

Procedure

17 (1.6 g, 3.08 mmol) was dissolved in dioxane (45 mL), transferred in a hydrogenation bottle and Pd on carbon (10%, 1.0 g) was added. Hydrogenation was done at 65 psi for 34 h. Following this period, additional Pd on carbon (10%, 0.6 g) was added and hydrogenation was allowed to continue for another 18 h. Catalyst was filtered through a bed of Celite® and solvent was evaporated. The residue was purified by column chromatography on reverse phase silica gel (C-18) using acetonitrile-water (1:1) mixture to elute 18 as white solid (0.60 g, 38%): mp 125-128° C.; 1H NMR (400 MHz, DMSO-d6) δ 12.04 (br s, 1H), 7.31 (d, J=8.4 Hz, 2H), 7.25 (d, J=8.4 Hz, 2H), 6.92 (d, J=8.6 Hz, 4H), 6.30 (d, J=2.0 Hz, 2H), 6.29 (t, J=2.0 Hz, 1H), 4.90 (dd, J=9.2 and 4.4 Hz, 1H), 3.98 (t, J=8.0 Hz, 1H), 3.67 (s, 6H), 3.56 (s, 3H), 3.37 (dd, J=13.6 and 4.0 Hz, 1H), 3.21 (dd, J=14.0 and 8.8 Hz, 1H); 3.11 (dd, J=14.0 and 9.2 Hz, 1H) and 2.90 (dd, J=13.6 and 7.6 Hz, 1H); MS (EI) m/z 522[M]+; Anal. (C28H27NO7S) C, H, N.

Workup

  1. additionwas added
  2. waitFollowing this period
  3. waitto continue for another 18 h
  4. filtrationCatalyst was filtered through a bed of Celite® and solvent
  5. customwas evaporated
  6. customThe residue was purified by column chromatography on reverse phase silica gel (C-18)
  7. washto elute 18 as white solid (0.60 g, 38%)

Sources & evidence

ORD record
ord-8848d9c5a21a4f2eadde4c38c434da35
Source dataset
uspto-grants-2008_08
Patent number
US07407978B2

Reaction notes

Loading…