(E)-4-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-2-methyl-but-3-enenitrile → 4-[3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-2-methyl-butyronitrile

HRID 660755Notes

Reaction equation

HRID 660755 reaction equation
C([O:8][C:9]1[CH:10]=[C:11](/[CH:23]=[CH:24]/[CH:25]([CH3:28])[C:26]#[N:27])[CH:12]=[CH:13][C:14]=1[N:15]1[CH2:19][C:18](=[O:20])[NH:17][S:16]1(=[O:22])=[O:21])C1C=CC=CC=1>CCOC(C)=O.CCO.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:10]=[C:11]([CH2:23][CH2:24][CH:25]([CH3:28])[C:26]#[N:27])[CH:12]=[CH:13][C:14]=1[N:15]1[CH2:19][C:18](=[O:20])[NH:17][S:16]1(=[O:22])=[O:21]

Participants

4

Reactant 1

HCID 68839915(E)-4-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-2-methyl-but-3-enenitrile

Product 1

HCID 577773284-[3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-2-methyl-butyronitrile

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A mixture of (E)-4-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-2-methyl-but-3-enenitrile (10 mg) and Pd(OH)2 (1 mg) in EtOAc/EtOH (3 mL) is hydrogenated at 1 atm for 2 h. The catalyst is filtered and the filtrate evaporated. The residue is washed with 1N HCl and the residue is purified by preparative HPLC to give the title compound: (M−1)−=308; HPLC retention time=0.78 min (method A).

Workup

  1. filtrationThe catalyst is filtered
  2. customthe filtrate evaporated
  3. washThe residue is washed with 1N HCl
  4. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-a69ea8861a2c43cdba995fd6e072b23b
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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