Benzyl glycinate → BOC-Ala-Gly-OBzl

HRID 436954Notes

Reaction equation

HRID 436954 reaction equation
ClC1C=C(Cl)C(Cl)=CC=1[O:10][C:11](=O)[C@H:12]([CH3:21])[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[CH2:23]([O:30][C:31](=[O:34])[CH2:32][NH2:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[CH2:23]([O:30][C:31](=[O:34])[CH2:32][NH:33][C:11](=[O:10])[C@H:12]([CH3:21])[NH:13][C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 409140Benzyl glycinateHCID 130552762,4,5-Trichlorophenyl N-(tert-butoxycarbonyl)-L-alaninate

Product 1

HCID 10980600BOC-Ala-Gly-OBzl

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

19.3 Parts N-t-butoxycarbonyl-L-alanine 2,4,5-trichlorophenyl ester and 9.7 parts glycine benzyl ester are dissolved in 200 parts methylene chloride and the resulting solution is stirred overnight at room temperature. Removal of the solvents under reduced pressure affords crude N-t-butoxycarbonyl-L-alanylglycine benzyl ester which is purified by low pressure column chromatography. The purified blocked dipeptide is then dissolved in 50 parts dioxane and stirred with a 10 fold excess of 2 N HCl in dioxane for 15 minutes. The solvent is removed by evaporation under reduced pressure to give, after trituration with ethyl ether, L-alanylglycine benzyl ester hydrochloride. This compound is represented by the following formula

Workup

  1. customRemoval of the solvents under reduced pressure

Sources & evidence

ORD record
ord-ada05b179f0643ed8a8f4efb9c123015
Source dataset
uspto-grants-1977_06
Patent number
US04028319

Reaction notes

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