5-{2-Benzyloxy-4-[2-(4-methoxybenzyloxy)-5-methylbenzyl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one → 5-[2-Benzyloxy-4-(2-hydroxy-5-methylbenzyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

HRID 660791Notes

Reaction equation

HRID 660791 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15][C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=2[O:23]CC2C=CC(OC)=CC=2)[CH:12]=[CH:11][C:10]=1[N:33]1[S:37](=[O:39])(=[O:38])[N:36]([CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[C:35](=[O:46])[CH2:34]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15][C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=2[OH:23])[CH:12]=[CH:11][C:10]=1[N:33]1[S:37](=[O:39])(=[O:38])[N:36]([CH2:40][CH2:41][Si:42]([CH3:43])([CH3:45])[CH3:44])[C:35](=[O:46])[CH2:34]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 688422585-{2-Benzyloxy-4-[2-(4-methoxybenzyloxy)-5-methylbenzyl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Product 1

HCID 667565515-[2-Benzyloxy-4-(2-hydroxy-5-methylbenzyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 5-{2-benzyloxy-4-[2-(4-methoxybenzyloxy)-5-methylbenzyl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (50 mg) in 10% TFA/methylene chloride (1 mL) is stirred at RT for 2 h. The solvent is removed under reduced pressure to give the title compound.

Workup

  1. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-b490be87810a44b2a68ec658df0013a9
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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