Sodium Hydroxide → HCID 57602440, compound

HRID 1787907Notes

Reaction equation

HRID 1787907 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:33]=[C:32]([N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[CH:31]=[CH:30][C:16]=2[C:17]([NH:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][C:25]=2[C:26]([O:28]C)=[O:27])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:33]=[C:32]([N:34]3[CH2:35][CH2:36][CH2:37][CH2:38]3)[CH:31]=[CH:30][C:16]=2[C:17]([NH:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][C:25]=2[C:26]([OH:28])=[O:27])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57602504HCID 57602504, compound

Product 1

HCID 57602440HCID 57602440, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-[2-(1-tert-butoxycarbonyl-piperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoylamino]pyridine-4-carboxylate (2.78 g, 5.3 mmol) in MeOH (100 mL) and THF (50 mL) was treated with 1 N NaOH (11 mL) and stirred at ambient temperature for 4 h. The reaction was quenched with glacial acetic acid (1 g) and concentrated to dryness. The residue was mixed with brine (50 mL) and extracted with 10% MeOH in CHCl3 (3×). The extracts were dried over MgSO4 and concentrated to 2.2 g (4.3 mmol, 81%) of a yellow solid.

Workup

  1. customThe reaction was quenched with glacial acetic acid (1 g)
  2. concentrationconcentrated to dryness
  3. additionThe residue was mixed with brine (50 mL)
  4. extractionextracted with 10% MeOH in CHCl3 (3×)
  5. dry with materialThe extracts were dried over MgSO4

Sources & evidence

ORD record
ord-484c18b173124ccca2ff61658cea3a7d
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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