Sodium Hydroxide → 5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)picolinic acid

HRID 711257Notes

Reaction equation

C[O:2][C:3]([C:5]1[N:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>O1CCOCC1.O>[C:20]([O:19][C:17]([N:14]1[CH2:13][CH2:12][N:11]([C:8]2[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[N:10][CH:9]=2)[CH2:16][CH2:15]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of tert-butyl 4-(6-(methoxycarbonyl)pyridin-3-yl)piperazine-1-carboxylate 49-3 (1.93 g, 6.01 mmol) and NaOH (530 mg, 13.26 mmol) in dioxane (15 mL) and H2O (15 mL) was stirred at 80° C. for 2 hours. Dioxane was removed by rotary evaporation and the resulting solution was acidified to pH around 4 by 1N HCl aqueous solution, followed by extraction with ethyl acetate (60 mL×3). The combined organic layers were washed with H2O and brine, dried over Na2SO4, and concentrated to dryness by rotary evaporation to afford 5-(4-(tert-butoxycarbonyl)piperazin-1-yl)picolinic acid 49-4 as a yellow solid. MS m/z 308.1 (M+1)

Workup

customDioxane was removed by rotary evaporation
extractionfollowed by extraction with ethyl acetate (60 mL×3)
washThe combined organic layers were washed with H2O and brine
dry with materialdried over Na2SO4
concentrationconcentrated to dryness by rotary evaporation

Sources & evidence

ORD record: ord-73030cce445e44a696ed75ac36ee1844
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181235B2

Reaction notes

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