5-[2-Benzyloxy-4-(3,3,3-trifluoropropyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one → 5-[2-Hydroxy-4-(3,3,3-trifluoropropyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660775Notes

Reaction equation

HRID 660775 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])[CH:12]=[CH:11][C:10]=1[N:21]1[S:25](=[O:27])(=[O:26])[N:24](CC[Si](C)(C)C)[C:23](=[O:34])[CH2:22]1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]([F:20])([F:18])[F:19])[CH:12]=[CH:11][C:10]=1[N:21]1[S:25](=[O:27])(=[O:26])[NH:24][C:23](=[O:34])[CH2:22]1

Participants

3

Reactant 1

HCID 689980165-[2-Benzyloxy-4-(3,3,3-trifluoropropyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Product 1

HCID 577773685-[2-Hydroxy-4-(3,3,3-trifluoropropyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

The title compound is prepared from 5-[2-benzyloxy-4-(3,3,3-trifluoropropyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one analogous to Example 292, steps B and C with the modification that Pd(OH)2 is used as the catalyst in the reduction step: (M−1)−=323.

Sources & evidence

ORD record
ord-56f0f0f5802e4cd5b665e928a5266148
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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