2-azidophenol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 450 mg of m-azidophenol (3.33 mmol), 407 mg pyruvic acid, 1.8 mg of pyridoxal-5'-phosphate, 711 mg of ammonium acetate and 10 units of tyrosine phenol lyase in 74 ml of water was adjusted to pH 8 with dilute NH4OH and stored in the dark at room temperature for 4 d. The mixture was then acidified with dilute acetic acid and filtered through celite. The filtrate was extracted two times with 50 ml of ethyl acetate to remove unreacted azidophenol [200 mg (1.48 mmol) azidophenol was recovered]. An Amberlite IRA-118H column (1.5×10 cm) activated with 2N HCl and washed with water. The reaction mixture was passed through the column and eluted with 4% NH4OH. The fractions that gave a positive ninhydrin reaction after spotting on silica gel plates were combined and lyophilized to give compound 1, 2-azido-L-tyrosine, as a white solid. Recrystallization from water gave 225 mg (1.01 mmol) of analytically pure 1, mp 200°-210° C. (decomp), [α]D23 -8.62 (C=4, 1N HCl), IR (KBr) cm-1 3700-2600, 2110, 1605, UV (H2O) λmax 219, 250, 290, ms (Cl NH3): 223 (M+1)+, 179 (M-COOH+1)+, 149 [HOPhN3 (CH3)]+, 1H NMR (D2O) 8 2.93 (1H, dd, J1 =14.5 Hz, J2 =8.2 Hz) , 3.20 (1H, dd, J1 =14.5 Hz, J2 =5.3 Hz) , 3.94 (1H, dd, J1 =8.2 Hz, J2 =5.3 Hz), 6.64 (1H, dd, J1 =8.3 Hz, J2 =2 Hz) , 6.75 (1H, d, J=2 Hz), 7.12 (H, d, J=8.3 Hz). dark at room temperature for 4 d filtered through celite The filtrate was extracted two times with 50 ml of ethyl acetate washed with water eluted with 4% NH4OH The fractions that gave