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

HRID 660714Notes

Reaction equation

HRID 660714 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([CH:15]2[CH:17]([CH2:18][CH2:19][CH2:20][CH3:21])[O:16]2)[CH:12]=[CH:11][C:10]=1[N:22]1[S:26](=[O:28])(=[O:27])[NH:25][C:24](=[O:29])[CH2:23]1)C1C=CC=CC=1>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:14]=[C:13]([CH2:15][CH:17]([OH:16])[CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[N:22]1[S:26](=[O:28])(=[O:27])[NH:25][C:24](=[O:29])[CH2:23]1

Participants

4

Reactant 1

HCID 866325855-[2-Benzyloxy-4-(3-butyloxiranyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Product 1

HCID 577773405-[2-Hydroxy-4-(2-hydroxyhexyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-[2-benzyloxy-4-(3-butyloxiranyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one (110 mg) and Pd(OH)2 (11 mg) in EtOAc (5 mL) is hydrogenated at 1 atm for 48 h. The catalyst is filtered and the filtrate evaporated. The residue is purified by preparative HPLC to give the title compound: (M−1)−=327; HPLC retention time=0.93 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-66f04418f2224ef68d1674c21298ebef
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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