Ammonia → tert-Butyl N-[4-(3-amino-3-oxopropyl)-2-pyridyl]carbamate

HRID 1828412Notes

Reaction equation

HRID 1828412 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]([OH:19])=O)[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:22](CC)CC)C.ClC(OCC)=O.N>O1CCCC1>[NH2:22][C:17](=[O:19])[CH2:16][CH2:15][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:14]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 220637293-{2-[(tert-Butoxycarbonyl)amino]-4-pyridyl)propanoic acid

Product 1

HCID 22063511tert-Butyl N-[4-(3-amino-3-oxopropyl)-2-pyridyl]carbamateYield 106%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-{2-[(tert-Butoxycarbonyl)amino]-4-pyridyl}propanoic acid (11.16 g, 41.92 mmol) dissolved in tetrahydrofuran (200 ml) was added with triethylamine (9 ml, 62.89 mmol), cooled with ice, and then added dropwise with ethyl chloroformate (6 ml, 62.89 mmol). The reaction mixture was stirred for 10 minutes, and then added with aqueous ammonia (50 ml) dissolved in tetrahydrofuran (50 ml) at 0° C. The reaction mixture was stirred for 20 minutes under ice cooling, and then the solvent was evaporated under reduced pressure. The resulting residue was washed with water and extracted with chloroform. The resulting organic layer was washed with saturated brine, and the organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain 11.794 g (100%) of the title compound as brown crystals without purification.

Workup

  1. temperaturecooled with ice
  2. stirringThe reaction mixture was stirred for 20 minutes under ice cooling
  3. customthe solvent was evaporated under reduced pressure
  4. washThe resulting residue was washed with water
  5. extractionextracted with chloroform
  6. washThe resulting organic layer was washed with saturated brine
  7. dry with materialthe organic layer was dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d35462f82eb462697301e392a270694
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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