Glycine → N-(2-hydroxybenzyl)glycine

Reaction equation

[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[CH:6](=O)[C:7]1[C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[OH:9].B.[Na]>[OH-].[Na+]>[OH:9][C:8]1[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=1[CH2:6][NH:1][CH2:2][C:3]([OH:5])=[O:4]

Participants

Procedure

Nine grams of glycine were dissolved in 60 ml of a 2N sodium hydroxide aqueous solution. To the solution were then added 12 ml of salicylaldehyde and 1.3 g of sodium boron hydride in this order. After the mixture was stirred for 1 hour, 12 ml of salicylaldehyde and 1.3 g of sodium boron hydride were added thereto again. After the resulting mixture was stirred at room temperature for 1 hour, the insoluble matter was separated through filtration, and the filtrate was extracted with diethyl ether. The extract was adjusted to a pH of 4 with hydrochloric acid to obtain 17 g of N-(2 -hydroxybenzyl) glycine. Various N-(2-hydroxybenzyl) amino acids were obtained in the same manner.