benzyl (2S)-2-aminopropanoate → Benzyl glycyl-L-alaninate hydrochloride

HRID 436953Notes

Reaction equation

HRID 436953 reaction equation
[Cl:1]C1C=C(Cl)C(Cl)=CC=1[O:10][C:11](=O)[CH2:12][NH:13]C(OC(C)(C)C)=O.[CH2:22]([O:29][C:30](=[O:34])[C@H:31]([CH3:33])[NH2:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[ClH:1].[CH2:22]([O:29][C:30](=[O:34])[C@H:31]([CH3:33])[NH:32][C:11](=[O:10])[CH2:12][NH2:13])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 726858benzyl (2S)-2-aminopropanoateHCID 12799284t-Butoxycarbonylglycine-2,4,5-Trichlorophenyl Ester

Product 1

HCID 53328828Benzyl glycyl-L-alaninate hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution containing 19.5 parts N-t-butoxycarbonylglycine 2,4,5-trichlorophenyl ester and 13.8 parts L-alanine benzyl ester in 200 parts methylene chloride is stirred overnight at room temperature. The solvent is then removed by evaporation under reduced pressure and the residue subjected to low pressure column chromatography. The resulting pure N-t-butoxycarbonylglycyl-L-alanine benzyl ester is dissolved in 60 parts dioxane and treated with a ten-fold excess of 2 N HCl in dioxane, with stirring, for 15 minutes. The solvent is again removed by evaporation under reduced pressure and the residue triturated with ethyl ether to afford glycyl-L-alanine benzyl ester hydrochloride. This compound is represented by the following formula

Workup

  1. customThe solvent is then removed by evaporation under reduced pressure
  2. dissolutionThe resulting pure N-t-butoxycarbonylglycyl-L-alanine benzyl ester is dissolved in 60 parts dioxane
  3. additiontreated with a ten-fold excess of 2 N HCl in dioxane
  4. stirringwith stirring, for 15 minutes
  5. customThe solvent is again removed by evaporation under reduced pressure
  6. customthe residue triturated with ethyl ether

Sources & evidence

ORD record
ord-4af204abe225464aa062b824a9e55eaa
Source dataset
uspto-grants-1977_06
Patent number
US04028319

Reaction notes

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