Sodium Hydroxide → 6-cyclopentyl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylic acid

HRID 505786Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505786
[CH:1]1([C:6]2[C:7]3[S:19][C:18]([C:20]([O:22]C)=[O:21])=[CH:17][C:8]=3[NH:9][C:10]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C1COCC1.CO>[CH:1]1([C:6]2[C:7]3[S:19][C:18]([C:20]([OH:22])=[O:21])=[CH:17][C:8]=3[NH:9][C:10]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 68470157methyl 6-cyclopentyl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Produkt 1

HCID 114497706-cyclopentyl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylic acidAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution (0.015 M) of methyl 6-cyclopentyl-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate in THF/MeOH (1:1) was treated with aqueous NaOH (2 N solution, 20 eq.) then the mixture was heated to reflux for 45 min. After cooling down, the mixture was concentrated then the residue diluted with water and acidified to pH 2-3 with aqueous HCl (1 N) and extracted with AcOEt. The combined organic phase was dried and concentrated to give a residue that was purified by RP-HPLC (Conditions: Waters X-TERRA MS C18, 10 micron, 19×150 mm; flow: 20 mL/min; Gradient: A: H2O+0.05% TFA; B: MeCN+0.05% TFA; 90% A isocratic for 2 min then linear to 10% A in 9 min) to afford the title compound (73%) as a solid.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 45 min
  3. temperatureAfter cooling down
  4. concentrationthe mixture was concentrated
  5. additionthe residue diluted with water
  6. extractionextracted with AcOEt
  7. customThe combined organic phase was dried
  8. concentrationconcentrated
  9. customto give a residue that
  10. customwas purified by RP-HPLC (Conditions

Quellen und Nachweise

ORD-Eintrag
ord-df0b3b3c98fa4182a0af729047a18306
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781431B2

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