HCID 67139624, compound → HCID 10194917, compound

HRID 1591980Notes

Reaction equation

HRID 1591980 reaction equation
[CH3:1][S:2]([C:5]1[CH:40]=[CH:39][C:8]([CH2:9][O:10][C:11](=[O:38])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:23][C:22](=[O:24])[N:21](CC4C=CC(OC)=CC=4OC)[S:20]3(=[O:37])=[O:36])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>C(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][O:10][C:11](=[O:38])[C:12]2[CH:13]=[CH:14][C:15]([CH2:18][N:19]3[CH2:23][C:22](=[O:24])[NH:21][S:20]3(=[O:36])=[O:37])=[CH:16][CH:17]=2)=[CH:39][CH:40]=1)(=[O:4])=[O:3]

Participants

3

Reactant 1

HCID 67139624HCID 67139624, compound

Product 1

HCID 10194917HCID 10194917, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

90 mg (150 μmol) of the title D compound, 4-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-benzoic acid 4-methanesulfonyl-benzyl ester are stirred in 4 mL of 1:1—TFA:CH2Cl2 for 50 min. The solvent is removed and the residue triturated with 4 mL of 1:1—MeCN:H2O. This mixture is filtered through a 0.2μ disk and the solvent is removed. The resulting material is purified by LC/MS and afforded 4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl)-benzoic acid 4-methanesulfonyl-benzyl ester: 1H-NMR (DMSO-d6) δ 3.22 (3H, s), 3.71 (2H, s), 4.27 (2H, s), 5.48 (2H, s), 7.54 (2H, d, J=8.1), 7.74 (2H, d, J=8.1), 7.96 (2H, d, J=8.5), 8.01 (2H, J=8.5); [M−1]−=437.

Workup

  1. customThe solvent is removed
  2. customthe residue triturated with 4 mL of 1
  3. filtrationThis mixture is filtered through a 0.2μ disk
  4. customthe solvent is removed
  5. customThe resulting material is purified by LC/MS

Sources & evidence

ORD record
ord-aa90ed190bd4411faf8ed4c35532749d
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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