Methanol → Methyl 4-((tert-butoxycarbonyl)amino)nicotinate

HRID 1823680

Reaction equation

HRID 1823680 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[CH:15]=[O:16])=[O:7])([CH3:4])[CH3:3].IN1C(=O)CCC1=O.C(=O)([O-])[O-].[K+].[K+].[O-]S([O-])(=S)=O.[Na+].[Na+].[CH3:38][OH:39]>>[CH3:38][O:39][C:15](=[O:16])[C:10]1[C:9]([NH:8][C:6]([O:5][C:2]([CH3:3])([CH3:1])[CH3:4])=[O:7])=[CH:14][CH:13]=[N:12][CH:11]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 819566tert-Butyl (3-formylpyridin-4-yl)carbamate

Product 1

HCID 23438729Methyl 4-((tert-butoxycarbonyl)amino)nicotinateYield 96%

Procedure

Formula 504 where R1, R3 and R4 are H; W, Y and Z are —C═; and X is —N═: To a solution of methanol (100 mL) and N-Boc-4-amino-3-pyridine carboxyaldehyde (8.3 g, 37.3 mmol), were added N-iodosuccinimide (21.0 g, 93.4 mmol) and potassium carbonate (12.9 g, 93.4 mmol) at room temperature. The mixture was stirred for 1 hour and then poured into a saturated Na2S2O3 solution (100 mL). After further dilution with water (100 mL) the mixture was extracted with dichloromethane (3×100 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to give the pure desired methyl ester product, 4-tert-butoxycarbonylamino-nicotinic acid methyl ester (9.0 g, 96%). MS (Cl) m/e: 253.1.

Workup

  1. extractionAfter further dilution with water (100 mL) the mixture was extracted with dichloromethane (3×100 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c93f853ac82e4cd486ec02c67ddde8f8
Source dataset
uspto-grants-2006_05
Patent number
US07038048B2

Linked notes

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