Lithium hydroxide, monohydrate → 5-Chloro-2-(3-((4-fluorophenoxy)methyl)azetidin-1-yl)nicotinic acid

HRID 72465Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:15][CH:14]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[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][CH:14]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:13]2)=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of methyl 5-chloro-2-(3-((4-fluorophenoxy)methyl)azetidin-1-yl)nicotinate (D82) (52.1 mg, 0.148 mmol) in a mixture (3:1) 1,4-dioxane/water (1.6 ml), lithium hydroxide monohydrate (9.3 mg, 0.22 mmol) was added and the resulting mixture was heated under microwave irradiation 6 min at 140° C. After solvent evaporation the residue was taken in a mixture water/1M HCl (20 ml/5 ml) and extracted with ethylacetate (3×20 ml). Collected organics after solvent evaporation afforded the title compound (D113) (55.4 mg).

Workup

customAfter solvent evaporation the residue
extractionextracted with ethylacetate (3×20 ml)
customCollected organics after solvent evaporation

Sources & evidence

ORD record: ord-3b10215cf9fa489581d259236e3b278f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828987B2

Reaction notes

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