Potassium Carbonate → HCID 57777464, compound

HRID 660682Notes

Reaction equation

HRID 660682 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C@@H:10]([NH:34][S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:37])=[O:36])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:22][C:21](=[O:23])[NH:20][S:19]2(=[O:25])=[O:24])=[C:14]([O:26]CC2C=CC=CC=2)[CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CCO.O.[Pd]>[NH:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[C@@H:10]([NH:34][S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:36])=[O:37])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:22][C:21](=[O:23])[NH:20][S:19]2(=[O:24])=[O:25])=[C:14]([OH:26])[CH:13]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 68839817HCID 68839817, compound

Product 1

HCID 57777464HCID 57777464, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19096565Water ethanolSolvent

Procedure

A solution of N-{(S)-1-(1H-benzoimidazol-2-yl)-2-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-ethyl}-benzenesulfonamide and K2CO3 (50 mg) in 10 mL of EtOH/water (1:1) is hydrogenated over 10% Pd/C (100 mg) at 1 atm for 18 h. The catalyst is filtered and the solvent is removed under reduced pressure. The residue is purified by reverse phase HPLC followed by lyophilization to give the title compound as a pink solid. (M−1)−: 526. HPLC retention time: 0.98 min. (Method A).

Workup

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

Sources & evidence

ORD record
ord-a5eba49c4a274f80b84c439c034ea5e4
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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