N-BOC-ethylenediamine → t-Butyl [2-(4-nitropyridine-2-carboxamido)ethyl]carbamate

HRID 34934Notes

Reaction equation

HRID 34934 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([OH:12])=O)[CH:5]=1)([O-:3])=[O:2].[NH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20]>O1CCCC1.C(N1C=CN=C1)(N1C=CN=C1)=O>[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([NH:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:12])[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 187201N-BOC-ethylenediamineHCID 27628254-Nitropicolinic Acid

Product 1

HCID 13800214t-Butyl [2-(4-nitropyridine-2-carboxamido)ethyl]carbamate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 682631,1'-CarbonyldiimidazoleSolvent

Procedure

6.0 g of 4-nitro-2-pyridinecarboxylic acid were stirred at 60° bath temperature for 4 hours in 300 ml of absolute tetrahydrofuran and 5.9 g of 1,1'-carbonyldiimidazole. Thereafter, 6.0 g of t-butyl (2-aminoethyl)carbamate were added thereto and the mixture was heated to reflux for 4 hours. The reaction mixture was concentrated under reduced pressure and thereafter partitioned between ethyl acetate and water. The combined organic phases were dried over magnesium sulfate and concentrated. The residue was crystallized from ethyl acetate, whereby there was obtained t-butyl [2-(4-nitropyridine-2-carboxamido)ethyl]carbamate as white crystals, m.p. 130°-131°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. custompartitioned between ethyl acetate and water
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-fdc7726315f94918a8ab532547c21886
Source dataset
uspto-grants-1988_08
Patent number
US04764522

Reaction notes

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