Sodium Hydroxide → HCID 11301804, compound

HRID 505829Notes

Reaction equation

HRID 505829 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:20]=[C:19]([C:21]([O:23]CC)=[O:22])[S:18][C:9]=3[NH:10][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[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[S:18][C:9]=3[NH:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68470346HCID 68470346, compound

Product 1

HCID 11301804HCID 11301804, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution (0.07 M) of ethyl 4-cyclohexyl-5-phenyl-6H-thieno[2,3-b]pyrrole-2-carboxylate in THF/MeOH (1:1) was treated with aqueous NaOH (2 N solution, 4 eq.). The mixture was heated to reflux for 6 hours. After cooling down, the reaction was concentrated and acidified to pH 1 with aqueous HCl (6 N). The resulting mixture was dissolved with DMSO and purified by RP-HPLC (Conditions: Waters X-TERRA MS C18, 5 micron, 19×150 mm; flow: 20 mL/min; Gradient: A: H2O+0.1% TFA; B: MeCN+0.1% TFA; linear from 95% A to 5% A in 10 min) to afford the title compound (54%) as a solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 hours
  3. temperatureAfter cooling down
  4. concentrationthe reaction was concentrated
  5. dissolutionThe resulting mixture was dissolved with DMSO
  6. custompurified by RP-HPLC (Conditions

Sources & evidence

ORD record
ord-083824b616524996a9514a0d1b5cf9aa
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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