3-{2-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-vinyl}-benzamide → 3-{2-[3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-ethyl}-benzamide

HRID 660481Notes

Reaction equation

HRID 660481 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][C:25]2[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=2)[C:28]([NH2:30])=[O:29])[CH:12]=[CH:13][C:14]=1[N:15]1[CH2:19][C:18](=[O:20])[NH:17][S:16]1(=[O:22])=[O:21])C1C=CC=CC=1>C(O)C.O.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH2:23][CH2:24][C:25]2[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=2)[C:28]([NH2:30])=[O:29])[CH:12]=[CH:13][C:14]=1[N:15]1[CH2:19][C:18](=[O:20])[NH:17][S:16]1(=[O:22])=[O:21]

Participants

5

Reactant 1

HCID 688385893-{2-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-vinyl}-benzamide

Product 1

HCID 167504543-{2-[3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-ethyl}-benzamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-{2-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-vinyl}-benzamide in ethanol (2 mL) is added two equivalents of KHCO3. The mixture is diluted with 5 mL water and hydrogenated at 1 atm over 50 mg of 10% Pd/C for 18 h. The catalyst is filtered and the filtrate lyophilized. The resulting solid is purified by HPLC to give the title compound as an amorphous powder: m/z (M−1)−=374; 1H NMR (DMSO-d6) δ 7.95 (m, 1H), 7.81 (s, 1H), 7.72 (m, 1H), 7.35 (m, 4H), 6.75 (d, J=1.5 Hz 1H), 6.70 (m, 1H), 4.04 (s, 2H), 2.86 (m, 4H).

Workup

  1. filtrationThe catalyst is filtered
  2. customThe resulting solid is purified by HPLC

Sources & evidence

ORD record
ord-4782873d91cd493aba25a87c734b3141
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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