Glycine → N-(p-nitrobenzyloxycarbonyl)glycine

HRID 744875Notes

Reaction equation

HRID 744875 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[N+:6]([C:9]1[CH:19]=[CH:18][C:12]([CH2:13][O:14][C:15](Cl)=[O:16])=[CH:11][CH:10]=1)([O-:8])=[O:7]>[OH-].[Na+].CCOCC>[N+:6]([C:9]1[CH:10]=[CH:11][C:12]([CH2:13][O:14][C:15]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:16])=[CH:18][CH:19]=1)([O-:8])=[O:7]

Participants

5

Reactant 2

HCID 750GlycineHCID 782054-Nitrobenzyl chloroformate

Product 1

HCID 12187147N-(p-nitrobenzyloxycarbonyl)glycine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

A 3.75 g portion of glycine was dissolved in 25 ml of 2N sodium hydroxide aqueous solution, and to the resulting solution cooled on an ice bath were simultaneously added in dropwise 10.77 g of p-nitrobenzyloxycarbonyl chloride dissolved in ether and 12.5 ml of 4N sodium hydroxide aqueous solution. After stirring at the same temperature for 2 hours, the reaction solution was washed with ether, the resulting aqueous layer was adjusted to acidic with concentrated hydrochloric acid, and the thus precipitated solid material was collected by filtration, washed with water and then dried to yield 11.98 g of N-(p-nitrobenzyloxycarbonyl)glycine as a white solid.

Workup

  1. temperatureto the resulting solution cooled on an ice bath
  2. washthe reaction solution was washed with ether
  3. filtrationthe thus precipitated solid material was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-736819ef050349cbb91368540c853e4f
Source dataset
uspto-grants-1996_09
Patent number
US05559224

Reaction notes

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