Diethyl Ether → HCID 70059617, compound

Temperature

0 °C

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.

1. stirringThe resulting solution was stirred overnight
2. washwashed sequentially with saturated aqueous NaHCO3 solution (20 mL) and brine (4×20 mL)
3. customThe organic phase was collected
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. customThe crude reaction product
7. customwas purified by chromatography (silica gel, 2:1 heptane/EtOAc)
8. customThe solid obtained
9. customwas crystallized from hot heptane
10. filtrationcollected by suction filtration
11. customdried

ORD record

ord-e0ea3705da364abbadc5e11464b48aa0

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06423689B1