Carbon Dioxide → 4-{[(Tert-butoxy)carbonyl]amino}pyridine-3-carboxylic acid

HRID 50773

Reaction equation

C([Li])CCC.[C:6]([O:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7].CCOCC.[C:25](=[O:27])=[O:26]>C1COCC1.C(O)(=O)C.O>[C:6]([O:10][C:11]([NH:13][C:14]1[C:15]([C:25]([OH:27])=[O:26])=[CH:16][N:17]=[CH:18][CH:19]=1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyl lithium (2.18 M, 24 mL, 52.51 mmol) is added slowly to a solution of 4-(N-t-butoxycarbonylamino)-pyridine (4.08 g, 21 mmol) in THF (50 mL, stirred under N2 at −78° C. The solution is allowed to warm to 0° C., stirred for 3 h, then cooled again to −78° C. and poured into ether (100 mL) containing dry ice. The solution is warmed to room temperature with constant stirring. Water is added and the mixture is neutralized with acetic acid. The resulting solid is collected by vacuum filtration and dried in a vacuum oven to give 4-(N-t-butoxycarbonylamino)nicotinic acid (2.72 g, 54%) as a brown solid. 1H NMR (DMSO) δ 11.75 (1H, brs), 8.95 (1H, s), 8.50 (1H, d, J=6.0 Hz) 8.20 (1H, d, J=6.0 Hz), 1.49 (9H, s).

Workup

temperatureto warm to 0° C.
stirringstirred for 3 h
temperaturecooled again to −78° C.
temperatureThe solution is warmed to room temperature with constant stirring
filtrationThe resulting solid is collected by vacuum filtration
customdried in a vacuum oven

Sources & evidence

ORD record: ord-b4e7f44004264174a2fd5c2c996aaf75
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713484B2

Linked notes

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