Trifluoroacetic acid → 4-(1,1,4-Trioxo-1,2,5-thiadiazolidin-2-ylmethyl)-benzoic acid 2-ethyl-butyl ester

HRID 1591985Notes

Reaction equation

HRID 1591985 reaction equation
[CH2:1]([CH:3]([CH2:34][CH3:35])[CH2:4][O:5][C:6](=[O:33])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH2:18][C:17](=[O:19])[N:16](CC3C=CC(OC)=CC=3OC)[S:15]2(=[O:32])=[O:31])=[CH:9][CH:8]=1)[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:34]([CH:3]([CH2:1][CH3:2])[CH2:4][O:5][C:6](=[O:33])[C:7]1[CH:8]=[CH:9][C:10]([CH2:13][N:14]2[CH2:18][C:17](=[O:19])[NH:16][S:15]2(=[O:31])=[O:32])=[CH:11][CH:12]=1)[CH3:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 671388714-[5-(2,4-Dimethoxy-benzyl)-1,1,4-trioxo1,2,5-thiadiazolidin-2-ylmethyl]-benzoic acid 2-ethyl-butyl ester

Product 1

HCID 102155084-(1,1,4-Trioxo-1,2,5-thiadiazolidin-2-ylmethyl)-benzoic acid 2-ethyl-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the title C compound, 4-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-benzoic acid 2-ethyl-butyl ester (230 mg, 0.456 mmol) and 2 mL of TFA in 6 mL of CH2Cl2 is stirred at RT overnight. The solvent is evaporated and the residue is treated with MeCN and filtered. The filtrate is concentrated and the residue is treated with Et2O, filtered and the Et2O is evaporated to give 4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl)-benzoic acid 2-ethyl-butyl ester as a light pink colored solid: [M−H]−=353.

Workup

  1. customThe solvent is evaporated
  2. additionthe residue is treated with MeCN
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated
  5. additionthe residue is treated with Et2O
  6. filtrationfiltered
  7. customthe Et2O is evaporated

Sources & evidence

ORD record
ord-20e2fd054a0c4b9db4b5aba5756520fc
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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