Methanol → 2-(5-Methyl-6-(4-(methylsulfonyl)phenylsulfonyl)-6H-thieno[2,3-b]pyrrol-4-yl)acetic acid

HRID 422579Notes

Reaction equation

HRID 422579 reaction equation
CO.O.[CH3:4][C:5]1[N:9]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[C:8]2[S:23][CH:24]=[CH:25][C:7]=2[C:6]=1[CH2:26][C:27]([O:29]C)=[O:28].[OH-].[K+]>CC(O)=O>[CH3:4][C:5]1[N:9]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)(=[O:11])=[O:12])[C:8]2[S:23][CH:24]=[CH:25][C:7]=2[C:6]=1[CH2:26][C:27]([OH:29])=[O:28]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14797Potassium HydroxideHCID 44176998Methyl 2-(5-methyl-6-(4-(methylsulfonyl)phenylsulfonyl)-6H-thieno[2,3-b]pyrrol-4-yl)acetate

Product 1

HCID 441887932-(5-Methyl-6-(4-(methylsulfonyl)phenylsulfonyl)-6H-thieno[2,3-b]pyrrol-4-yl)acetic acidYield 14.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Methanol (0.5 mL) and water (0.5 mL) were added to the crude methyl 2-(5-methyl-6-(4-(methylsulfonyl)phenylsulfonyl)-6H-thieno[2,3-b]pyrrol-4-yl)acetate, followed by the addition of KOH (47.5 mg, 0.846 mmol). The mixture was stirred at ambient temperature for 1 h before adding the AcOH (0.66 mL). The reaction mixture was dried under reduced pressure (Genevac®) and the residue purified by HPLC (Table 1, Method g) to afford the title compound (0.017 g, 14.6%): LC/MS (Table 1, Method b) Rt=1.89 min; MS m/z 412 (M−H)−; 1H NMR (DMSO) δ 8.19-8.08 (m, 4H), 7.23 (d, 1H, J=5.28 Hz), 6.96 (d, 1H, J=5.28 Hz), 3.41 (s, 2H), 3.29 (s, 3H), 2.37 (s, 3H).

Workup

  1. customThe reaction mixture was dried under reduced pressure (Genevac®)
  2. customthe residue purified by HPLC (Table 1, Method g)

Sources & evidence

ORD record
ord-7f7a353692724f86bac4f1ec3b9d7122
Source dataset
uspto-grants-2012_01
Patent number
US08101645B2

Reaction notes

Loading…