4-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-3,3-dimethylbutyronitrile → 4-[3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-3,3-dimethylbutyronitrile

HRID 660759Notes

Reaction equation

HRID 660759 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH2:23][C:24]([CH3:29])([CH3:28])[CH2:25][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.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:10]=[C:11]([CH2:23][C:24]([CH3:29])([CH3:28])[CH2:25][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 688387924-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-3,3-dimethylbutyronitrile

Product 1

HCID 577774334-[3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-3,3-dimethylbutyronitrile

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-3,3-dimethylbutyronitrile (25 mg) and Pd(OH)2 (25 mg) in EtOAc (5 mL) is hydrogenated at 1 atm for 6 h. The catalyst is filtered and the filtrate evaporated. The residue is purified by preparative HPLC to give the title compound: (M−1)−=322.

Workup

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

Sources & evidence

ORD record
ord-3050bd41cc0f4fd5bbc625bab4450a2b
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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