4-Methoxybenzyl azidoformate → 2-Methylene-5-(p-methoxybenzyloxycarbonyl)aminopentanoic acid

HRID 262790Notes

Reaction equation

HRID 262790 reaction equation
Cl.[CH2:2]=[C:3]([CH2:7][CH2:8][CH2:9][NH2:10])[C:4]([OH:6])=[O:5].[O-2].[Mg+2].[CH3:13][O:14][C:15]1[CH:27]=[CH:26][C:18]([CH2:19][O:20][C:21](N=[N+]=[N-])=[O:22])=[CH:17][CH:16]=1>O.O1CCOCC1>[CH2:2]=[C:3]([CH2:7][CH2:8][CH2:9][NH:10][C:21]([O:20][CH2:19][C:18]1[CH:26]=[CH:27][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1)=[O:22])[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

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

Product 1

HCID 135481222-Methylene-5-(p-methoxybenzyloxycarbonyl)aminopentanoic acidYield 116.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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 of ethyl acetate, two equivalents of Dowex 50 ion exchange resin
  3. additionis 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-da04f3905531415eb984758043879873
Source dataset
uspto-grants-1979_05
Patent number
US04154946

Reaction notes

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