Triethylamine → 3-(4-Benzyloxy-phenyl)-2-(2-methanesulfonylamino-4-methyl-pentanoylamino)-propionic acid tert-butyl ester

A solution of the product from Example AI ([S-(R*,R*)]-2-{2-amino-4-methyl-pentanoylamino}-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester) (0.25 g, 1.7 mmol) and triethylamine (0.5 mL) in CH2Cl2 (10 mL) was treated with methansulfonyl chloride (0.25 mL). The resulting solution was stirred overnight at room temperature. The reaction mixture was treated with ethyl acetate (100 mL) and washed sequentially with aqueous 1N HCl solution (3×20 mL), saturated aqueous NaHCO3 solution (3×20 mL), and brine (3×20 mL). The organic phase was dried (MgSO4), filtered, and concentrated. The residue was purified by chromatography (silica gel, 1:1 ethyl acetate/heptane) to give the title compound as a pale peach powder (0.15 g, 51%), mp=83-84° C.

1. washwashed sequentially with aqueous 1N HCl solution (3×20 mL), saturated aqueous NaHCO3 solution (3×20 mL), and brine (3×20 mL)
2. dry with materialThe organic phase was dried (MgSO4)
3. filtrationfiltered
4. concentrationconcentrated
5. customThe residue was purified by chromatography (silica gel, 1:1 ethyl acetate/heptane)

ORD record

ord-4bb87cb0d07d46acb9a98dfa4e627a25

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06423689B1