HCID 68839254, compound → HCID 57777358, compound

HRID 660632Notes

Reaction equation

HRID 660632 reaction equation
[CH3:1][O:2][C:3](=[O:47])[C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:5]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:46])/[C:18](/[NH:42][C:43](=[O:45])[CH3:44])=[CH:19]\[C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:30][C:29](=[O:31])[NH:28][S:27]2(=[O:33])=[O:32])=[C:22]([O:34]CC2C=CC=CC=2)[CH:21]=1>CCO.CC(O)=O.[Pd]>[CH3:1][O:2][C:3](=[O:47])[C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:5]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:46])[CH:18]([NH:42][C:43](=[O:45])[CH3:44])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:30][C:29](=[O:31])[NH:28][S:27]2(=[O:32])=[O:33])=[C:22]([OH:34])[CH:21]=1

Participants

4

Reactant 1

HCID 68839254HCID 68839254, compound

Product 1

HCID 57777358HCID 57777358, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18476134Acetic acid ethanolSolvent

Procedure

A solution of 2-(4-{(E)-2-acetylamino-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acryloylamino}-butoxy)-6-hydroxybenzoic acid methyl ester (300 mg) in 16 mL of EtOH/HOAc (1:1) is hydrogenated 1 atm over 10% Pd/C (70 mg) for 4 h. The catalyst is filtered, the solvent is removed under reduced pressure. The residue is purified by reverse phase HPLC and lyophilization to give the title compound as a white solid. This is converted to its potassium salt by addition of 1 equivalent of KHCO3: (M−1)−=577. HPLC retention time: 0-86 min. (Method A).

Workup

  1. customfor 4 h
  2. filtrationThe catalyst is filtered
  3. customthe solvent is removed under reduced pressure
  4. customThe residue is purified by reverse phase HPLC and lyophilization

Sources & evidence

ORD record
ord-0e3451e243054c33a0e7e0da090e0e57
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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