Sodium Hydroxide → Azido-PEG1-CH2CO2H

HRID 355253Notes

Reaction equation

HRID 355253 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][C:8]([O:10]CC)=[O:9])=[N+:2]=[N-:3].[OH-].[Na+]>CO>[N:1]([CH2:4][CH2:5][O:6][CH2:7][C:8]([OH:10])=[O:9])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20452089HCID 20452089, compound

Product 1

HCID 13663206Azido-PEG1-CH2CO2HYield 77.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-azidoethoxyacetate (6.56 g, 37.9 mmol) in MeOH (80 ml) was added 1N aq. NaOH (80 ml) and the mixture was stirred at room temperature overnight (17 h). After removing the insoluble material, the methanol was evaporated in vacuo and this was saturated with sodium chloride and washed with ether (30 ml×3). The aqueous layer acidified with 3N HCl (30 ml) was extracted with ether (40 ml×4). The ether extracts were washed with brine, dried (MgSO4) and evaporated to yield 4.25 g (29.3 mmol, 77.3%) of 2-azidoethoxyacetic acid as a colourless oil: 1Hmr (CDCl3) δ: 3.3-4.0 (4H, m, --OCH2CH2N3), 4.22 (2H, s, --COCH2O--), 9.52 ppm (1H, s, --CO2H, exchanged with D2O); ir (neat) νmax : 2600-3300 (br,--CO 2 H) 2100 (azide) and 1740 cm-1C=O--CO2H). This material was used in the next step without further purification.

Workup

  1. customAfter removing the insoluble material
  2. customthe methanol was evaporated in vacuo
  3. washthis was saturated with sodium chloride and washed with ether (30 ml×3)
  4. extractionwas extracted with ether (40 ml×4)
  5. washThe ether extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-856d22d81e2c4ba0a373ee3b0e1cc673
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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