Water → 5-(4-Cyclopentylmethyl-2-hydroxyphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660777Notes

Reaction equation

HRID 660777 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([CH2:15][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:12]=[CH:11][C:10]=1[N:21]1[S:25](=[O:27])(=[O:26])[NH:24][C:23](=[O:28])[CH2:22]1)C1C=CC=CC=1.O>CCO.[Pd]>[CH:16]1([CH2:15][C:13]2[CH:12]=[CH:11][C:10]([N:21]3[S:25](=[O:27])(=[O:26])[NH:24][C:23](=[O:28])[CH2:22]3)=[C:9]([OH:8])[CH:14]=2)[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 2

HCID 962WaterHCID 688388965-(2-Benzyloxy-4-cyclopentylmethylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Product 1

HCID 577773615-(4-Cyclopentylmethyl-2-hydroxyphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-(2-benzyloxy-4-cyclopentylmethylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one in EtOH (2 mL)/water (6 mL) is hydrogenated at 1 atm over 10% Pd/C for 18 h. The catalyst is filtered and the filtrate evaporated. The residue is purified by preparative HPLC to give the title compound: (M−1)−=309. HPLC retention time: 1.14 min. (Method A).

Workup

  1. filtrationThe catalyst is filtered
  2. customthe filtrate evaporated
  3. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-3682a2b9226d44ee87cff786bb78ae16
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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