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231958-14-8

231958-14-8 Structure

231958-14-8 Structure
IdentificationBack Directory
[Name]

6-[(TERT-BUTOXYCARBONYL)AMINO]NICOTINIC ACID
[CAS]

231958-14-8
[Synonyms]

6-Aminonicotinic acid, N-BOC protected
6-Aminonicotinic acid, 6-BOC protected
6-[(TERT-BUTOXYCARBONYL)AMINO]NICOTINIC ACID
6-{[(tert-butoxy)carbonyl]amino}pyridine-3-carboxylic acid
6-[(2-methylpropan-2-yl)oxycarbonylamino]pyridine-3-carboxylic acid
3-Pyridinecarboxylic acid, 6-[[(1,1-dimethylethoxy)carbonyl]amino]-
6-[(tert-Butoxycarbonyl)amino]pyridine-3-carboxylic acid, 2-[(tert-Butoxycarbonyl)amino]-5-carboxypyridine
[Molecular Formula]

C11H14N2O4
[MDL Number]

MFCD02682388
[MOL File]

231958-14-8.mol
[Molecular Weight]

238.24
Chemical PropertiesBack Directory
[Melting point ]

292-296°C
[Boiling point ]

356.5±27.0 °C(Predicted)
[density ]

1.293±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,Room Temperature
[form ]

Solid
[pka]

12.92±0.70(Predicted)
[Appearance]

White to off-white Solid
Safety DataBack Directory
[Hazard Codes ]

Xi
[HazardClass ]

IRRITANT
[HS Code ]

2933399990
Spectrum DetailBack Directory
[Spectrum Detail]

6-[(TERT-BUTOXYCARBONYL)AMINO]NICOTINIC ACID(231958-14-8)1HNMR
Hazard InformationBack Directory
[Synthesis]

METHYL 6-[(TERT-BUTOXYCARBONYL)AMINO]NICOTINATE

144186-11-8

6-[(TERT-BUTOXYCARBONYL)AMINO]NICOTINIC ACID

231958-14-8

Step 5. Synthesis of 6-((tert-butoxycarbonyl)amino)nicotinic acid. Methyl 6-((tert-butoxycarbonyl)amino)nicotinate (50 g, 19 mmol) was dissolved in methanol (50 mL) and 1N NaOH aqueous solution (40 mL, 40 mmol) was added. The reaction mixture was stirred at room temperature for 20 hours, followed by heating to 60°C for 2 hours. After completion of the reaction, the solution was cooled and methanol was removed under vacuum. To the remaining solution, 3N HCl was slowly added and the pH was adjusted to 3. A white solid precipitate was precipitated. The solid product was collected by filtration, washed with water and dried to give 6-((tert-butoxycarbonyl)amino)nicotinic acid 23 g (89% yield) as a white solid.

[References]

[1] Patent: WO2010/130708, 2010, A1. Location in patent: Page/Page column 72
[2] Patent: WO2010/144345, 2010, A1. Location in patent: Page/Page column 65
[3] Patent: WO2016/33445, 2016, A1. Location in patent: Paragraph 0297
[4] Patent: WO2009/36996, 2009, A2. Location in patent: Page/Page column 92
[5] Patent: EP3305785, 2018, A1. Location in patent: Paragraph 0233
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