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

HRID 569875Notes

Reaction equation

HRID 569875 reaction equation
Cl.[CH2:2]=[C:3]([CH2:7][CH2:8][CH2:9][NH2:10])[C:4]([OH:6])=[O:5].O.[O-2].[Mg+2].[CH3:14][O:15][C:16]1[CH:28]=[CH:27][C:19]([CH2:20][O:21][C:22](N=[N+]=[N-])=[O:23])=[CH:18][CH:17]=1>O1CCOCC1>[CH2:2]=[C:3]([CH2:7][CH2:8][CH2:9][NH:10][C:22]([O:21][CH2:20][C:19]1[CH:27]=[CH:28][C:16]([O:15][CH3:14])=[CH:17][CH:18]=1)=[O:23])[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 1175214-Methoxybenzyl azidoformateHCID 6850729Magnesium monoxideHCID 127744252-Methylene-5-aminopentanoic acid hydrochloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 8.8 g. of 2-methylene-5-aminopentanoic acid hydrochloride in 100 ml. of water is added with stirring 6.36 g. of magnesium oxide, followed by a solution of 12.2 g. of p-methoxybenzyloxycarbonyl azide in 100 ml. of dioxane, and the resulting mixture is stirred at room temperature for two days. The reaction mixture is filtered, and the filtrate diluted with 200 ml. of ethyl acetate, two equivalents of Dowex 50 ion exchange resin is added, and the mixture is stirred at room temperature for two hours. The resin is then filtered off and washed with water. The layers in the filtrate are separated and the aqueous layer is extracted twice with ethyl acetate. The combined organic layers are dried and concentrated in vacuo to give 18.2 g of 2-methylene-5-(p-methoxybenzyloxycarbonyl)aminopentanoic acid as an amber oil which crystallizes on standing. This is used without further purification.

Workup

  1. filtrationThe reaction mixture is filtered
  2. additionthe filtrate diluted with 200 ml
  3. additionof ethyl acetate, two equivalents of Dowex 50 ion exchange resin is added
  4. stirringthe mixture is stirred at room temperature for two hours
  5. filtrationThe resin is then filtered off
  6. washwashed with water
  7. customThe layers in the filtrate are separated
  8. extractionthe aqueous layer is extracted twice with ethyl acetate
  9. customThe combined organic layers are dried
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b62eb52ed4cc451b9c4b6cfa138e503d
Source dataset
uspto-grants-1988_03
Patent number
US04734420

Reaction notes

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