Sodium Hydroxide → 6-(Cyclopropylmethoxy)-5-(tetrahydrofuran-2-yl)-pyridine-2-carboxylic acid

HRID 632145Notes

Reaction equation

HRID 632145 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:15][CH2:14][O:13][CH2:12]2)=[C:7]([O:16][CH2:17][CH:18]2[CH2:20][CH2:19]2)[N:6]=1)=[O:4].C[O:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([CH:31]2[CH2:35][CH2:34][CH2:33][O:32]2)=[C:27]([O:36][CH2:37][CH:38]2[CH2:40][CH2:39]2)[N:26]=1)=[O:24].[OH-].[Na+]>C(O)C>[CH:18]1([CH2:17][O:16][C:7]2[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[CH:9][C:8]=2[CH:11]2[CH2:15][CH2:14][O:13][CH2:12]2)[CH2:19][CH2:20]1.[CH:38]1([CH2:37][O:36][C:27]2[N:26]=[C:25]([C:23]([OH:24])=[O:22])[CH:30]=[CH:29][C:28]=2[CH:31]2[CH2:35][CH2:34][CH2:33][O:32]2)[CH2:39][CH2:40]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 710874556-(Cyclopropylmethoxy)-5-(tetrahydrofuran-3-yl)-pyridine-2-carboxylic acid methyl esterHCID 710877676-(Cyclopropylmethoxy)-5-(tetrahydrofuran-2-yl)-pyridine-2-carboxylic acid methyl ester

Product 2

HCID 710873686-(Cyclopropylmethoxy)-5-(tetrahydrofuran-2-yl)-pyridine-2-carboxylic acidYield 100%HCID 710873756-(Cyclopropylmethoxy)-5-(tetrahydrofuran-3-yl)-pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-(cyclopropylmethoxy)-5-(tetrahydrofuran-3-yl)-pyridine-2-carboxylic acid methyl ester (c1) and 6-(cyclopropylmethoxy)-5-(tetrahydrofuran-2-yl)-pyridine-2-carboxylic acid methyl ester (c2) (mixture from Example 114 c, 0.35 g, 1.3 mmol) and sodium hydroxide (55 mg, 1.4 mmol) in ethanol (50 mL) was heated to 90° C. for 2 h. The reaction mixture was evaporated, dissolved in water and extracted with ethyl acetate (30 mL). The pH of the aqueous layer was adjusted to 2 by addition of 1 N hydrochloric acid and the resulting precipitate was collected by filtration and dried in vacuo to give 6-(cyclopropylmethoxy)-5-(tetrahydrofuran-3-yl)-pyridine-2-carboxylic acid (d1) and 6-(cyclopropylmethoxy)-5-(tetrahydrofuran-2-yl)-pyridine-2-carboxylic acid (d2) (mixture, d1:d2=3:2, 0.33 g, 1.3 mmol, 100%) as yellow solid; MS (EI): m/e=264.2 [M+H]+.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutiondissolved in water
  3. extractionextracted with ethyl acetate (30 mL)
  4. additionThe pH of the aqueous layer was adjusted to 2 by addition of 1 N hydrochloric acid
  5. filtrationthe resulting precipitate was collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e0f95f83fa1c4abc8f8c769e7cfede69
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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