تفاعل #52906

معادلة التفاعل

2-thienylboronic acid

K2CO3

N-(tert-butoxycarbonyl)-O-(trifluoromethanesulfonyl)-L-tyrosine methyl ester

→

N-(tert-butoxycarbonyl)-4-(2-thienyl)-L-phenylalanine methyl ester

المردود 62.6%

المذيبات

toluene DMF

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىwas purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1:3)

الإجراء التجريبي

To a mixture of 2-thienylboronic acid (1.135 g) and anhydrous K2CO3 (2.23 g) in toluene/DMF (75 mL/7.5 mL) under N2 was added a solution of N-(tert-butoxycarbonyl)-O-(trifluoromethanesulfonyl)-L-tyrosine methyl ester (3.42 g) in 5 mL of toluene. Pd(PPh3)4 (1.4 g) was added and the mixture was heated at 80° C. for 24 h. After usual work-up as shown in Example 1 the crude material was purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1:3) to yield N-(tert-butoxycarbonyl)-4-(2-thienyl)-L-phenylalanine methyl ester (1.81 g). ESMS: m/z 362 (MH+).

المصدر