Acetic Acid → Methyl 4-((tert-butoxycarbonyl)amino)nicotinate

HRID 1787923Notes

Reaction equation

HRID 1787923 reaction equation
[C:1]([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[C:15]([OH:17])=[O:16])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:18][Si](C=[N+]=[N-])(C)C.C(O)(=O)C>CO>[C:1]([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[C:15]([O:17][CH3:18])=[O:16])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 221726234-{[(Tert-butoxy)carbonyl]amino}pyridine-3-carboxylic acid

Product 1

HCID 23438729Methyl 4-((tert-butoxycarbonyl)amino)nicotinateYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring suspension of 4-(Boc-amino)pyridine-3-carboxylic acid (1.04 g, 4.37 mmol) in methanol (3.5 mL) was added a 2 M solution of (trimethylsilyl)diazomethane in hexanes (3.5 mL, 7 mmol). After 15 min, acetic acid was added and the solvents were removed in vacuo. The residue was chromatographed over silica gel, eluting with a step gradient of 20% ethyl acetate in hexanes through 70% ethyl acetate in hexanes. The product containing fractions were combined and concentrated in vacuo to give the title compound (0.894 g, 81%) as a white solid.

Workup

  1. customthe solvents were removed in vacuo
  2. customThe residue was chromatographed over silica gel
  3. washeluting with a step gradient of 20% ethyl acetate in hexanes through 70% ethyl acetate in hexanes
  4. additionThe product containing fractions
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5347db7719614c68834cfe16e6710679
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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