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

HRID 505786ノート

反応式

HRID 505786 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-df0b3b3c98fa4182a0af729047a18306
出典データセット
uspto-grants-2010_08
特許番号
US07781431B2

反応ノート

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