Tiopronin → 2-[2-[[2-[(4-Sulfamoylphenyl)carbamoyl]phenyl]disulfanyl]propanoylamino]acetic acid

HRID 583530

Reaction equation

HRID 583530 reaction equation
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][N:3]1[C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH2:20])(=[O:19])=[O:18])=[CH:13][CH:12]=1.[SH:21][CH:22]([CH3:30])[C:23]([NH:25][CH2:26][C:27]([OH:29])=[O:28])=[O:24]>>[S:17]([C:14]1[CH:15]=[CH:16][C:11]([NH:3][C:2]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][S:21][CH:22]([CH3:30])[C:23]([NH:25][CH2:26][C:27]([OH:29])=[O:28])=[O:24])=[O:1])=[CH:12][CH:13]=1)(=[O:19])(=[O:18])[NH2:20]

Participants

3

Reactant 2

HCID 5483TioproninHCID 4629384-(3-Oxo-1,2-benzothiazol-2-yl)benzenesulfonamide

Product 1

HCID 64835592-[2-[[2-[(4-Sulfamoylphenyl)carbamoyl]phenyl]disulfanyl]propanoylamino]acetic acidYield 92.3%

Procedure

This compound was prepared according to the method of Example 132 using 0.46 g (1.5 mmol) of 4-(3-oxo-3H-benzo[d]isothiazol-2-yl)benzenesulfonamide and 0.25 g (1.5 mmol) of 2-mercapto-propionylglycine. The product was washed with ether and dried in vacuo to give 0.65 g of the title compound, mp 254-256° C.

Workup

  1. customThis compound was prepared
  2. washThe product was washed with ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-a27834f9303744768d6ea5f76cd6a5e4
Source dataset
uspto-grants-1999_07
Patent number
US05929114

Linked notes

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