HCID 68838962, compound → HCID 57777409, compound

HRID 660707Notes

Reaction equation

HRID 660707 reaction equation
[CH2:1]([CH:8]([C:32](=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[S:20](=[O:22])(=[O:21])[NH:19][C:18](=[O:23])[CH2:17]2)=[C:12]([O:24]CC2C=CC=CC=2)[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.O.[Pd]>[CH2:1]([CH:8]([C:32](=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[S:20](=[O:22])(=[O:21])[NH:19][C:18](=[O:23])[CH2:17]2)=[C:12]([OH:24])[CH:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 68838962HCID 68838962, compound

Product 1

HCID 57777409HCID 57777409, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19096565Water ethanolSolvent

Procedure

A mixture of 5-[4-(2-benzyl-3-oxo-3-phenylpropyl)-2-benzyloxyphenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one (40 mg, 0.069 mmol) and 7 mg of Degussa 5% Pd/C in 4 mL of ethanol/water (1:1) is hydrogenated at 1 atm for 8 h at RT. The catalyst is filtered through Celite, washed with 1:1 ethanol/water and the filtrate concentrated under reduced pressure. The resulting residue is stripped four times with ethanol and the resulting solid is triturated with ether and dried to afford the title compound as a solid: (M−1)−=449. HPLC retention time=0.88 min (Method C).

Workup

  1. filtrationThe catalyst is filtered through Celite
  2. washwashed with 1:1 ethanol/water
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customthe resulting solid is triturated with ether
  5. customdried

Sources & evidence

ORD record
ord-b55be8dbde6947c29094a63b501d034a
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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