Sodium Hydroxide → 5-(4-chlorophenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylic acid

HRID 505810Notes

Reaction equation

HRID 505810 reaction equation
C(OC([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]C)=[O:30])=[CH:28][C:9]1=2)=O)(C)(C)C.[OH-].[Na+]>C(Cl)Cl.C(O)(C(F)(F)F)=O.CO>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C:12]2[NH:8][C:9]3[CH:28]=[C:27]([C:29]([OH:31])=[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

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68467133methyl 4-(tert-butoxycarbonyl)-5-(4-chlorophenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 113718275-(4-chlorophenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylic acidYield 53%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution (0.5 M) of methyl 4-(tert-butoxycarbonyl)-5-(4-chlorophenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate in DCM/TFA (1:1) was stirred at RT for 1 h. Evaporation of the solvent gave a solid that was dissolved in MeOH. The resulting solution (0.1N) was treated with aqueous NaOH (1 N solution, 12 eq.). The mixture was heated to reflux for 3 h then concentrated and acidified to pH 1 with aqueous HCl (1 N), the aqueous solution was diluted with MeCN and purified by RP-HPLC (Conditions: Waters X-TERRA MS C18, 5 micron, 19×150 mm; flow: 15 mL/min; Gradient: A: H2O+0.05% TFA; B: MeCN+0.05% TFA; 60% A isocratic for 2 min then linear to 0% A in 10 min) to afford the title compound (53%) as a solid.

Workup

  1. customEvaporation of the solvent
  2. customgave a solid
  3. temperatureThe mixture was heated
  4. temperatureto reflux for 3 h
  5. concentrationthen concentrated
  6. additionthe aqueous solution was diluted with MeCN
  7. custompurified by RP-HPLC (Conditions

Sources & evidence

ORD record
ord-f11bed82b8554d69a24c74dc3afea7c0
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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