Sodium Hydroxide → 6-Cyclohexyl-4-(methoxymethyl)-5-phenyl-thieno[3,2-b]pyrrole-2-carboxylic acid

HRID 505788Notes

Reaction equation

HRID 505788 reaction equation
[CH:1]1([C:7]2[C:8]3[S:23][C:22]([C:24]([O:26]C)=[O:25])=[CH:21][C:9]=3[N:10]([CH2:18][O:19][CH3:20])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C1COCC1.CO>[CH:1]1([C:7]2[C:8]3[S:23][C:22]([C:24]([OH:26])=[O:25])=[CH:21][C:9]=3[N:10]([CH2:18][O:19][CH3:20])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68471693methyl 6-cyclohexyl-4-(methoxymethyl)-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 497740056-Cyclohexyl-4-(methoxymethyl)-5-phenyl-thieno[3,2-b]pyrrole-2-carboxylic acidYield 93%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution (0.1 M) of methyl 6-cyclohexyl-4-(methoxymethyl)-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate in THF/MeOH (1:1) was treated with aqueous NaOH (1 N solution, 5 eq.). The mixture was stirred at RT for 21 h then concentrated and acidified to pH 4-5 with aqueous HCl (1 N) and extracted with AcOEt. The combined organic phase was dried and concentrated to give a residue that was triturated with MeCN/Et2O (20:1) and filtered to afford the title compound (93%) as a solid.

Workup

  1. concentrationthen concentrated
  2. extractionextracted with AcOEt
  3. customThe combined organic phase was dried
  4. concentrationconcentrated
  5. customto give a residue that
  6. customwas triturated with MeCN/Et2O (20:1)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-89928a590af5409184fdb91d6e2a0191
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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