Trifluoroacetic acid → 5-(4-amino-benzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one TFA salt

HRID 1591967Notes

Reaction equation

HRID 1591967 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[CH2:19][C:18](=[O:20])[N:17](CC3C=CC(OC)=CC=3OC)[S:16]2(=[O:33])=[O:32])=[CH:10][CH:9]=1)(C)(C)C.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>C(Cl)Cl>[OH:41][C:35]([C:37]([F:40])([F:39])[F:38])=[O:36].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[S:16](=[O:33])(=[O:32])[NH:17][C:18](=[O:20])[CH2:19]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67138359HCID 67138359, compound

Product 1

HCID 865910365-(4-amino-benzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one TFA salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the title C compound, {4-[5-(2,4-dimethoxybenzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]phenyl}carbamic acid t-butyl ester (20 mg, 0.041 mmol) in CH2Cl2 (1 mL) is added TFA (1 mL). The reaction is stirred at RT overnight. Upon addition the reaction becomes light pink colored, progressing to deep purple after overnight. The solvent is evaporated and the residue is taken up in 2 mL of MeCN/water (50/50). This is filtered through a 0.2 micron PTFE membrane filter and the filtrate is collected. MeCN is removed under reduced pressure and water via lyophilization to give 5-(4-amino-benzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one TFA salt as a yellow foam: [M−1]−=240.

Workup

  1. additionUpon addition the reaction
  2. customdeep purple after overnight
  3. customThe solvent is evaporated
  4. filtrationThis is filtered through a 0.2 micron PTFE membrane
  5. filtrationfilter
  6. customthe filtrate is collected
  7. customMeCN is removed under reduced pressure and water via lyophilization

Sources & evidence

ORD record
ord-0a54b86ee6c1473288d4fd36673d0236
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

Loading…