2-Mercaptobenzoic Acid → HCID 19023680, compound

HRID 1034265Notes

Reaction equation

HRID 1034265 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9](SC(C)(C)C)=[C:8]2[CH2:23][C:24]([CH3:30])([CH3:29])[C:25]([O:27][CH3:28])=[O:26])=[CH:4][CH:3]=1.C(O)(=O)C1C(=CC=CC=1)S>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH2:23][C:24]([CH3:30])([CH3:29])[C:25]([O:27][CH3:28])=[O:26])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 54432-Mercaptobenzoic AcidHCID 117625003-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid methyl ester

Product 1

HCID 19023680HCID 19023680, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of the product from Step 1 (2.03 g, 4.29 mmol) and thiosalicylic acid (1.32 g, 8.58 mmol) in TFA (25 mL) was refluxed for 2.5 hours. The TFA was evaporated, the residue was diluted with EtOAc, washed twice with 1N aq NaOH, then 3× with H2O, dried and evaporated to afford the crude title product as a thick oil which was taken as such into the next step.

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. customThe TFA was evaporated
  3. additionthe residue was diluted with EtOAc
  4. washwashed twice with 1N aq NaOH
  5. dry with material3× with H2O, dried
  6. customevaporated

Sources & evidence

ORD record
ord-eef482d2ece7407dad948dc4a4163547
Source dataset
uspto-grants-1994_05
Patent number
US05314898

Reaction notes

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