Triethylamine → (2-t-Butoxycarbonylaminoethyl)carbamic acid p-nitrobenzyl ester

HRID 891739Notes

Reaction equation

HRID 891739 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][N:10]=[N+]=[N-])([CH3:4])([CH3:3])[CH3:2].[N+:14]([C:17]1[CH:27]=[CH:26][C:20]([CH2:21][O:22][C:23](Cl)=[O:24])=[CH:19][CH:18]=1)([O-:16])=[O:15].C(N(CC)CC)C>CO.[OH-].[OH-].[Pd+2]>[N+:14]([C:17]1[CH:18]=[CH:19][C:20]([CH2:21][O:22][C:23](=[O:24])[NH:10][CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:13])=[CH:26][CH:27]=1)([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 782054-Nitrobenzyl chloroformateHCID 22323692tert-Butyl (2-azidoethyl)carbamate

Product 1

HCID 69543921(2-t-Butoxycarbonylaminoethyl)carbamic acid p-nitrobenzyl esterYield 66%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of (2-azidoethyl)carbamic acid t-butyl ester (1.22 g, 6.55 mmol) in methanol (60 ml) was subjected to catalytic hydrogenation in the presence of 20% palladium hydroxide on charcoal (1.22 g) at room temperature. After checking the completion of the reaction, the reaction mixture was filtered, and the filtrate concentrated under reduced pressure. To a solution of the obtained crude product in methylene chloride (60 ml) were added chloroformic acid p-nitrobenzyl ester (2.12 g, 9.8 mmol) and triethylamine (1.37 ml, 9.8 mmol) in an ice bath, and the reaction mixture was stirred at room temperature overnight. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using toluene:acetonitrile (3:1) as the eluant to afford (2-t-butoxycarbonylaminoethyl)carbamic acid p-nitrobenzyl ester (1.46 g, yield 66%) as a white solid.

Workup

  1. customthe completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customTo a solution of the obtained crude product in methylene chloride (60 ml)
  5. customthe completion of the reaction
  6. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-1ff3addd19014d2a8f55b7f2c963d36e
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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