Diethyl Ether → 2-(2-(p-Nitrobenzyloxycarbonylamino)ethoxy)acetic acid

HRID 744884Notes

Reaction equation

HRID 744884 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][C:6]([OH:8])=[O:7].CCOCC.C(=O)(O)[O-].[Na+].[N+:19]([C:22]1[CH:32]=[CH:31][C:25]([CH2:26][O:27][C:28](Cl)=[O:29])=[CH:24][CH:23]=1)([O-:21])=[O:20]>O>[N+:19]([C:22]1[CH:23]=[CH:24][C:25]([CH2:26][O:27][C:28]([NH:1][CH2:2][CH2:3][O:4][CH2:5][C:6]([OH:8])=[O:7])=[O:29])=[CH:31][CH:32]=1)([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 782054-Nitrobenzyl chloroformateHCID 516892Sodium BicarbonateHCID 111709562-(2-aminoethoxy)acetic Acid

Product 1

HCID 194224242-(2-(p-Nitrobenzyloxycarbonylamino)ethoxy)acetic acidYield 99.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

With cooling on an ice bath, to 596 mg of 2-(2-aminoethoxy)acetic acid dissolved in 10 ml of water was added an ether solution of 883 mg sodium bicarbonate and 1.29 g p-nitrobenzyloxycarbonyl chloride in dropwise manner. After stirring the reaction solution for 17 hours at room temperature, the resulting aqueous layer was collected, adjusted to acidic with concentrated hydrochloric acid and extracted with ethyl acetate, and the resulting organic layer was washed with water and dried over sodium sulfate, followed by evaporation of the solvent under a reduced pressure to yield 1.48 g of 2-(2-(p-nitrobenzyloxycarbonylamino)ethoxy)acetic acid.

Workup

  1. customthe resulting aqueous layer was collected
  2. extractionextracted with ethyl acetate
  3. washthe resulting organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. customfollowed by evaporation of the solvent under a reduced pressure

Sources & evidence

ORD record
ord-f465f527d76741e7a902e9a2b2ca4341
Source dataset
uspto-grants-1996_09
Patent number
US05559224

Reaction notes

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