Ethanol → 3-[2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoylamino]thiophene-2-carboxylic Acid

HRID 1787913Notes

Reaction equation

HRID 1787913 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:32]=[C:31]([N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)[CH:30]=[CH:29][C:16]=2[C:17]([NH:19][C:20]2[CH:24]=[CH:23][S:22][C:21]=2[C:25]([O:27]C)=[O:26])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCO.[OH-].[K+]>O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:32]=[C:31]([N:33]3[CH2:34][CH2:35][CH2:36][CH2:37]3)[CH:30]=[CH:29][C:16]=2[C:17]([NH:19][C:20]2[CH:24]=[CH:23][S:22][C:21]=2[C:25]([OH:27])=[O:26])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 57602470HCID 57602470, compound

Product 1

HCID 576024853-[2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoylamino]thiophene-2-carboxylic AcidYield 94.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the methyl 3-[2-(1-tert-butoxycarbonyl-piperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoylamino]-thiophene-2-carboxylate (3.8 g, 7.2 mmol) and EtOH (100 mL) was treated with a solution of KOH (0.88 g) in water (80 mL). The reaction mixture was refluxed overnight, quenched with glacial acetic acid (1.5 mL) and concentrated under vacuum. The resulting aqueous mixture was extracted with EtOAc (2×100 mL). The combined extracts were dried over MgSO4 and concentrated to give 3.5 g (6.8 mmol, 94%) of the acid as a foam.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customquenched with glacial acetic acid (1.5 mL)
  3. concentrationconcentrated under vacuum
  4. extractionThe resulting aqueous mixture was extracted with EtOAc (2×100 mL)
  5. dry with materialThe combined extracts were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e4eb1700d8884e7e92062637cba3ef88
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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