Sodium Hydroxide → 3-[5-Chloro-6-(cyano-dimethyl-methyl)-pyridin-3-yl]-propionic acid

HRID 2387119Notes

Reaction equation

C([O:3][C:4](=[O:19])[CH2:5][CH2:6][C:7]1[CH:8]=[N:9][C:10]([C:14]([C:17]#[N:18])([CH3:16])[CH3:15])=[C:11]([Cl:13])[CH:12]=1)C.[OH-].[Na+]>C1COCC1.O>[Cl:13][C:11]1[CH:12]=[C:7]([CH2:6][CH2:5][C:4]([OH:19])=[O:3])[CH:8]=[N:9][C:10]=1[C:14]([C:17]#[N:18])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of 3-[5-chloro-6-(cyano-dimethyl-methyl)-pyridin-3-yl]-propionic acid ethyl ester (0.68 g, 2.43 mmol) from step 4 above, in 1:1 THF/H2O (4 mL) was added 2 N NaOH (2.43 mL). The resulting solution was stirred at 60° C. for 1 hour. Solvents were removed and residue was partitioned between ethyl acetate and 10% citric acid and extracted. The organic phase was washed with brine (50 mL), dried over Na2SO4 and evaporated. The residue solidified to a white solid and was used without further purification. (0.39 g, 64%) as a white solid. ESIMS (MH−): 251.

Workup

customSolvents were removed
customresidue was partitioned between ethyl acetate and 10% citric acid
extractionextracted
washThe organic phase was washed with brine (50 mL)
dry with materialdried over Na2SO4
customevaporated
customwas used without further purification

Sources & evidence

ORD record: ord-7a086f3aa17342c28851030ed7023a36
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268835B2

Reaction notes

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