Acetic acid ethanol → N-{4-[3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-butyl}-phthalamic Acid

HRID 660591Notes

Reaction equation

HRID 660591 reaction equation
C([O:8][C:9]1[CH:10]=[C:11](/[CH:23]=[CH:24]/[CH2:25][CH2:26][N:27]2[C:35](=[O:36])[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]2=[O:37])[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.CC[OH:40].CC(O)=O>[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:35](=[O:36])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([OH:37])=[O:40])[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

4

Reactant 2

HCID 18476134Acetic acid ethanolHCID 688427202-{(E)-4-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-but-3-enyl}-isoindole-1,3-dione

Product 1

HCID 57777344N-{4-[3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-butyl}-phthalamic Acid

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 2-{(E)-4-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-but-3-enyl}-isoindole-1,3-dione (70 mg, 0.135 mmol) in 6 mL of EtOH/HOAc (4:2) is hydrogenated at 50 psi over 10% Pd/C (70 mg) for 18 h. The catalyst is filtered, the solvent is removed under reduced pressure and the residual yellow foam triturated with EtOAc to give the title compound as a solid: (M−1)−=446.

Workup

  1. filtrationThe catalyst is filtered
  2. customthe solvent is removed under reduced pressure
  3. customthe residual yellow foam triturated with EtOAc

Sources & evidence

ORD record
ord-dd80f985888b45d690e9c17f0d319c6f
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

Loading…