methyl 4-(2-tert-butoxy-2-oxoethyl)-6-cyclohexyl-5-(4-chlorophenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate → [5-(4-chlorophenyl)-6-cyclohexyl-2-(methoxycarbonyl)-5-phenyl-4H-thieno[3,2-b]pyrrol-4-yl]acetic acid

HRID 505812Notes

Reaction equation

HRID 505812 reaction equation
C([O:5][C:6](=[O:33])[CH2:7][N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:11]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:10]2[S:26][C:27]([C:29]([O:31][CH3:32])=[O:30])=[CH:28][C:9]1=2)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C:12]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:8]([CH2:7][C:6]([OH:5])=[O:33])[C:9]3=[CH:28][CH:27]([C:29]([O:31][CH3:32])=[O:30])[S:26][C:10]3=[C:11]2[CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)=[CH:18][CH:17]=1

Participants

3

Reactant 1

HCID 68467870methyl 4-(2-tert-butoxy-2-oxoethyl)-6-cyclohexyl-5-(4-chlorophenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 68470301[5-(4-chlorophenyl)-6-cyclohexyl-2-(methoxycarbonyl)-5-phenyl-4H-thieno[3,2-b]pyrrol-4-yl]acetic acidYield 94%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution (0.04 M) of methyl 4-(2-tert-butoxy-2-oxoethyl)-6-cyclohexyl-5-(4-chlorophenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate in DCM/TFA (1:1) was stirred at RT for 3 h. Evaporation of the solvent gave the title compound (94%) as a solid.

Workup

  1. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e4d4b12a1bc943cf8c5034032af18e13
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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