Water → HCID 57777330, compound

HRID 660750Notes

Reaction equation

HRID 660750 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][CH2:17][CH2:18][S:19](CC2C=CC=CC=2)(=[O:21])=[O:20])[CH:12]=[CH:11][C:10]=1[N:29]1[S:33](=[O:35])(=[O:34])[NH:32][C:31](=[O:36])[CH2:30]1)C1C=CC=CC=1.O>CCO.[Pd]>[OH:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][CH2:17][CH2:18][S:19]([OH:21])=[O:20])[CH:12]=[CH:11][C:10]=1[N:29]1[CH2:30][C:31](=[O:36])[NH:32][S:33]1(=[O:35])=[O:34]

Participants

5

Reactant 2

HCID 962WaterHCID 68871536HCID 68871536, compound

Product 1

HCID 57777330HCID 57777330, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-[2-benzyloxy-4-(4-phenylmethanesulfonylbutyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one (450 mg), 10% Pd/C (400 mg) and KHCO3 (1.6 mL of 0.52M) in EtOH (1 mL)/water (10 mL) is hydrogenated at 1 atm for 2 h. The catalyst is filtered and the filtrate evaporated. The residue is treated with 1N HCl and extracted with EtOAc. The organic phase is dried over magnesium sulfate and the solvent removed under reduced pressure to give the title compound: (M−1)−=347 1H NMR (400 MHz, DMSO-D6) δ ppm 1.38-1.48 (m, 2 H) 1.49-1.58 (m, J=7.67, 7.67, 7.52, 7.20 Hz, 3 H) 1.79-1.85 (m, 2 H) 2.43 (t, J=7.45 Hz, 2 H) 4.01 (s, 2 H) 6.56 (dd, J=8.08, 1.77 Hz, 1 H) 6.67 (d, J=1.77 Hz, 1 H) 7.25 (d, J=8.08 Hz, 1 H)

Workup

  1. filtrationThe catalyst is filtered
  2. customthe filtrate evaporated
  3. additionThe residue is treated with 1N HCl
  4. extractionextracted with EtOAc
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-6f1d7aca1d614245ae8f6686cf7b557b
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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