反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
A solution of BOC-O-(2,6-dichlorobenzyl)-L-tyrosine (Bachem, 2.00 g, 4.54 mmol) in 20 mL of DMF and iPr2NEt (1.6 mL) was cooled to 0° C. and treated with HBTU (1.72 g, 4.54 mmol). The resulting solution was stirred at 0° C. for 30 minutes and treated with tert-butyl amine (0.48 mL, 4.54 mmol). The resulting solution was stirred overnight. The reaction mixture was poured into ether (100 mL) and washed sequentially with saturated aqueous NaHCO3 solution (20 mL) and brine (4×20 mL). The organic phase was collected and dried (MgSO4) and concentrated. The crude reaction product was purified by chromatography (silica gel, 2:1 heptane/EtOAc). The solid obtained was crystallized from hot heptane, collected by suction filtration and dried to give the title compound as a white solid (1.56 g, 69%), mp=82-86° C.
WORKUP
后处理
- stirringThe resulting solution was stirred overnight
- washwashed sequentially with saturated aqueous NaHCO3 solution (20 mL) and brine (4×20 mL)
- customThe organic phase was collected
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe crude reaction product
- customwas purified by chromatography (silica gel, 2:1 heptane/EtOAc)
- customThe solid obtained
- customwas crystallized from hot heptane
- filtrationcollected by suction filtration
- customdried