L-Tyrosine → N-formyl-L-tyrosine

反応式

[NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[C:14](OC(=O)C)(=[O:16])C>C(O)=O.O>[CH:14]([NH:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:16]

参加物

反応条件

温度: 10 °C

実験手順

L-Tyrosine (60 g; 0.33 mol) was dissolved in 98% formic acid (400 ml) and cooled to 10° C. Acetic anhydride, (192 ml; 1.73 mol) was added in four stages for five minutes, while at the same time maintaining a temperature of 10° C. The mixture was then stirred for 60 min at 10° C. and then kept at room temperature for 30 min. Water (192 ml) was added with stirring at 10 to 15° C. for 30 min, and then the mixture was subjected to evaporation under reduced pressure at 70° C., until a dry residue was obtained. The residual oily solid was dissolved in a minimal volume of boiling water, and then cooled to produce fine white crystals of N-formyl-L-tyrosine (60.6 g; 88%).