반응 #52906

반응 방정식

2-thienylboronic acid

K2CO3

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

→

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

수율 62.6%

용매

toluene DMF

toluene

반응 조건

후처리

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

실험 절차

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+).

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