2-((E)-2-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-vinyl)-piperidine-1-carboxylic Acid Tert-butyl Ester → HCID 68842724, compound

HRID 660583Notes

Reaction equation

HRID 660583 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:26][C:25](=[O:27])[N:24]([CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[S:23]2(=[O:35])=[O:34])=[C:18]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:17]=1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH2:37]([O:36][C:18]1[CH:17]=[C:16](/[CH:15]=[CH:14]/[CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]2)[CH:21]=[CH:20][C:19]=1[N:22]1[S:23](=[O:34])(=[O:35])[N:24]([CH2:28][CH2:29][Si:30]([CH3:31])([CH3:33])[CH3:32])[C:25](=[O:27])[CH2:26]1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

3

Reactant 1

HCID 688384762-((E)-2-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-vinyl)-piperidine-1-carboxylic Acid Tert-butyl Ester

Product 1

HCID 68842724HCID 68842724, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 2-((E)-2-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-vinyl)-piperidine-1-carboxylic acid tert-butyl ester (Example 62, step B) (240 mg, 0.353 mmol) in TFA/methylene chloride (3:8) is stirred at RT for 75 min. The solvent is removed under reduced pressure and the residue purified by preparative HPLC to give the title compound.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-d938dde272de495da38147dcb07d037d
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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