4-(5-Tert-butoxy-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid ethyl ester → 4-(5-Hydroxy-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid ethyl ester

HRID 2215995Notes

Reaction equation

HRID 2215995 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([S:31][CH3:32])=[C:9]([S:11]([C:14]2[CH:15]=[C:16]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:17]=[C:18]([O:20]C(C)(C)C)[CH:19]=2)(=[O:13])=[O:12])[CH:10]=1)=[O:5])[CH3:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([S:31][CH3:32])=[C:9]([S:11]([C:14]2[CH:15]=[C:16]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:17]=[C:18]([OH:20])[CH:19]=2)(=[O:13])=[O:12])[CH:10]=1)=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 695864274-(5-Tert-butoxy-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid ethyl ester

Product 1

HCID 695866254-(5-Hydroxy-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid ethyl esterYield 100.4%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

4-(5-tert-butoxy-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid ethyl ester (55 mg, 0.11 mmol) was dissolved in 1:1 TFA/DCM (10 mL) and stirring for 1 h. Removal of the solvent in vacuo yielded the title compound (48 mg, 98%), which was used without further purification.

Workup

  1. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-d2bad043728a47428c3f49cd008cf984
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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