Water → 2-Methylene-5-(p-methoxybenzyloxycarbonyl)aminopentanoic acid

HRID 485630Notes

Reaction equation

HRID 485630 reaction equation
[OH2:1].[O-2:2].[Mg+2].[CH3:4][O:5][C:6]1[CH:18]=[CH:17][C:9]([CH2:10][O:11][C:12]([N:14]=[N+]=[N-])=[O:13])=[CH:8][CH:7]=1>O1CCOCC1>[CH2:10]=[C:9]([CH2:8][CH2:7][CH2:6][NH:14][C:12]([O:11][CH2:10][C:9]1[CH:17]=[CH:18][C:6]([O:5][CH3:4])=[CH:7][CH:8]=1)=[O:13])[C:17]([OH:2])=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 1175214-Methoxybenzyl azidoformateHCID 6850729Magnesium monoxide

Product 1

HCID 135481222-Methylene-5-(p-methoxybenzyloxycarbonyl)aminopentanoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3.8 grams (53 mmol) of the product from part E in 100 ml. of water were added 6.4 grams (159 mmol) of magnesium oxide with stirring followed by a solution of 12.2 grams (59 mmol) of p-methoxybenzyloxycarbonyl azide in 100 ml. of p-dioxane. The resulting slurry was stirred at room temperature for two days. The mixture then was filtered through Hyflo and diluted with 200 ml. of ethyl acetate. AG50W-X2 Dowex 50 ion-exchange resin (200 ml. wet volume) was added, and the mixture was stirred at room temperature for 2 hours. The resin then was removed by filtration and washed with water. The filtrate layers were separated, and the aqueous layer was extracted twice with 200 ml. of ethyl acetate. The combined ethyl acetate solution was dried over magnesium sulfate and concentrated in vacuo to give 15.5 grams of the title compound as an oil.

Workup

  1. stirringThe resulting slurry was stirred at room temperature for two days
  2. filtrationThe mixture then was filtered through Hyflo
  3. additiondiluted with 200 ml
  4. additionAG50W-X2 Dowex 50 ion-exchange resin (200 ml. wet volume) was added
  5. stirringthe mixture was stirred at room temperature for 2 hours
  6. customThe resin then was removed by filtration
  7. washwashed with water
  8. customThe filtrate layers were separated
  9. extractionthe aqueous layer was extracted twice with 200 ml
  10. dry with materialThe combined ethyl acetate solution was dried over magnesium sulfate
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d311369f455549bf98f981be06f3e731
Source dataset
uspto-grants-1985_08
Patent number
US04537727

Reaction notes

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