tert-Butanol → Ethyl 6-[(tert-butoxycarbonyl)amino]pyridine-2-carboxylate

HRID 2244413Notes

Reaction equation

HRID 2244413 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8](C(O)=O)[N:7]=1)=[O:5])[CH3:2].C([N:17]([CH2:20]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.[C:39]([OH:43])([CH3:42])([CH3:41])[CH3:40]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:17][C:20]([O:43][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:29])[N:7]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 35944446-(Ethoxycarbonyl)picolinic acid

Product 1

HCID 19349079Ethyl 6-[(tert-butoxycarbonyl)amino]pyridine-2-carboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of pyridine-2,6-dicarboxylic acid monoethyl ester (1.00 g, 5.12 mmol), triethylamine (1.04 g, 10.24 mmol), diphenylphosphoryl azide (DPPA) (1.93 g, 7.02 mmol) and tert-butanol (3.00 ml) in toluene (30.00 ml) was warmed at 100° C. for 20 h. The mixture was then cooled at room temperature, diluted with ethyl acetate and washed with saturated sodium bicarbonate and brine. The organic layer was then dried over sodium sulphate and evaporated. The residue was purified by flash chromatography to yield 6-tert-butoxycarbonylamino-pyridine-2-carboxylic acid ethyl ester (1.06 g, 78%) as a viscous orange oil, MS (ISP): m/e=267.3 (M+H+).

Workup

  1. washwashed with saturated sodium bicarbonate and brine
  2. dry with materialThe organic layer was then dried over sodium sulphate
  3. customevaporated
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-dc32e2909aef4fe6adb1df949762e70f
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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