Lithium hydroxide, monohydrate → HCID 22939410, compound

HRID 1774013Notes

Reaction equation

HRID 1774013 reaction equation
C([O:3][C:4](=[O:14])[CH:5]([CH3:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)C.O.[OH-].[Li+]>O1CCOCC1.O>[CH3:13][CH:5]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[C:4]([OH:14])=[O:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22939391HCID 22939391, compound

Product 1

HCID 22939410HCID 22939410, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (±)-2-methyl-3-pyridin-2-yl-propionic acid ethyl ester (250 mg, 1.29 mmol, 1.0 eq.) in dioxane (8 mL), lithium hydroxide monohydrate (67 mg, 1.55 mmol, 1.2 eq.) in water (5 mL) was added in portions keeping the temperature below 30° C. The resulting solution was stirred at r.t. for 18 hours. The mixture was concentrated in vacuo The residue was dissolved in water (3 mL), MeCN (1 mL) and formic acid (0.5 mL). The solution was directly purified by prep. HPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions, extremely polar method) and concentrated in vacuo to give the title compound as a white solid.

Workup

  1. customthe temperature below 30° C
  2. concentrationThe mixture was concentrated in vacuo The residue
  3. dissolutionwas dissolved in water (3 mL)
  4. customThe solution was directly purified by prep
  5. concentrationHPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions, extremely polar method) and concentrated in vacuo

Sources & evidence

ORD record
ord-2a5859baa4384235a174c0058c9e928f
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

Loading…