Water → HCID 68833121, compound

HRID 1787926Notes

Reaction equation

HRID 1787926 reaction equation
[C:1]([C:5]1[CH:23]=[CH:22][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[C:18]([O:20]C)=[O:19])=[O:10])=[C:7]([O:24][CH:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O.[Li+].[OH-]>O1CCCC1>[C:1]([C:5]1[CH:23]=[CH:22][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[C:18]([OH:20])=[O:19])=[O:10])=[C:7]([O:24][CH:25]2[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29][CH2:30]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962Water2×HCID 3939Lithium HydroxideHCID 68831591HCID 68831591, compound

Product 1

HCID 68833121HCID 68833121, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of methyl 4-[4-tert-butyl-2-(1-Boc-piperidin-4-yloxy)benzoylamino]pyridine-3-carboxylate (0.192 g, 0.376 mmol) in tetrahydrofuran (4 mL) was added water (1 mL), followed by a 1 M solution of LiOH in water (0.4 mL, 0.4 mmol). After stirring overnight, the solution was partially concentrated in vacuo and then diluted with water and washed with diethyl ether. The pH of the aq phase was then adjusted to 4-5 by the addition of citric acid. The resulting precipitate was dried in vacuo to give the title compound (0.15 g, 80%) as a white solid.

Workup

  1. concentrationthe solution was partially concentrated in vacuo
  2. additiondiluted with water
  3. washwashed with diethyl ether
  4. additionThe pH of the aq phase was then adjusted to 4-5 by the addition of citric acid
  5. customThe resulting precipitate was dried in vacuo

Sources & evidence

ORD record
ord-7348ba2905634b879e85a0d88faa1132
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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