ethanol ether 1 2 and cooled to give 22 4 g 84 of a crystalline solid m p 104 u00b0 6 u00b0 a solution of the active ester 0 048 mole 22 4 g and dibenzyldopamine hcl 0 048 mole 17 8 g in 100 ml of dmf was treated with triethylamine 0 1 mole 14 ml and stirred at room temperature for 4 hours the solution was then diluted with water to give an oil which solidified on standing the white solid was collected and washed well with water the moist solid was dissolved in boiling absolute ethanol filtered and allowed to crystallize the solid was collected and washed with ethanol to give after drying at 60 u00b0 overnight 29 4 g of the protected amide m p 126 u00b0 8 u00b0 ______________________________________microanalysis for c sub 42 h sub 42 n sub 2 o sub 7 molecular weight 686 8calc found ______________________________________c 73 45 73 52h 6 16 6 27n 4 08 4 13______________________________________ a suspension of the protected amide 0 0365 mole 25 g from step 2 was reduced in a parr apparatus in ethanol containing 5 0 g 5 pd c and 1 eq of concentrated hcl after uptake was complete the catalyst was filtered and washed with ethanol the filtrate was concentrated in vacuo to give upon repeated azeotroping with methanol a glass this glass was dried under high vacuum at 60 u00b0 for 24 hours to give 11 3 g 97 of n 5 u03b2 3 4 dihydroxyphenyl ethyl glutamine hcl ______________________________________microanalysis for c sub 13 h sub 19 cln sub 2 o sub.