Gamma-Aminobutyric Acid → 4-(p-Nitrobenzyloxycarbonyl)aminobutyric acid

HRID 744877

Reaction equation

HRID 744877 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[N+:8]([C:11]1[CH:21]=[CH:20][C:14]([CH2:15][O:16][C:17](Cl)=[O:18])=[CH:13][CH:12]=1)([O-:10])=[O:9]>[OH-].[Na+].CCOCC>[N+:8]([C:11]1[CH:12]=[CH:13][C:14]([CH2:15][O:16][C:17]([NH:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6])=[O:18])=[CH:20][CH:21]=1)([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 119Gamma-Aminobutyric AcidHCID 782054-Nitrobenzyl chloroformate

Product 1

HCID 31025414-(p-Nitrobenzyloxycarbonyl)aminobutyric acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

A 3.10 g portion of 4-aminobutyric acid was dissolved in 15 ml of 2N sodium hydroxide, to the solution were simultaneously added dropwise 6.48 g of p-nitrobenzyloxycarbonyl chloride dissolved in ether and 7.5 ml of 4N sodium hydroxide while cooling on an ice-bath. After 2 hours of stirring at the same temperature, the solution was washed with ether, the resulting aqueous layer was adjusted to acidic with concentrated hydrochloric acid, and a precipitated. solid material was collected by filtration, washed with water and then dried to yield 7.64 g of 4-(p-nitrobenzyloxycarbonyl)aminobutyric acid.

Workup

  1. washthe solution was washed with ether
  2. filtrationsolid material was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-76df18d0f4d64a038a34fc97e55f1999
Source dataset
uspto-grants-1996_09
Patent number
US05559224

Linked notes

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