Lithium hydroxide, monohydrate → HCID 67958667, compound

HRID 72464Notes

Reaction equation

HRID 72464 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)([OH:16])[CH2:13]2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].O.[OH-].[Li+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)([OH:16])[CH2:13]2)=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67958212Methyl 5-chloro-2-(3-(3-fluorophenyl)-3-hydroxyazetidin-1-yl)nicotinate

Product 1

HCID 67958667HCID 67958667, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 5-chloro-2-(3-(3-fluorophenyl)-3-hydroxyazetidin-1-yl)nicotinate (D80) (70 mg, 0.207 mmol) in a mixture 3:1 1,4-dioxane/water (2 ml), lithium hydroxide monohydrate (133 mg, 0.312 mmol) was added and the resulting mixture was stirred 4 h at 70° C. After solvent evaporation the residue was taken in a mixture water/1M HCl (10 ml/10 ml) and extracted with ethylacetate (2×30 ml). Collected organics after solvent evaporation afforded the title compound (D111) (64.6 mg).

Workup

  1. customAfter solvent evaporation the residue
  2. extractionextracted with ethylacetate (2×30 ml)
  3. customCollected organics after solvent evaporation

Sources & evidence

ORD record
ord-4583d85b1bb14058979520e1d8da1ae0
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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