Benzylamine → N-Benzyl-L-serinamide

Temperature

0 °C

To a mixture of 4.10 g (20 mmol) of N-Boc-L-serine, 2.97 g (22 mmol) of HOBT, 2.42 mL (22 mmol) of NMM, and 2.40 mL (22 mmol) of benzylamine in 50 mL of anhydrous DMF at 0° C. was added 4.21 g of WSC. The mixture was stirred at 0° C. for 1 h and at room temperature for 3 h. This was then taken up in 300 mL of EtOAc and washed with 100 mL of H2O (2×) and brine (1×). The combined organic layers were dried over MgSO4 and concentrated. After drying under vacuum overnight, the residue was dissolved in 20 mL of CH2Cl2 and treated with 20 mL of CF3CO2H at 0-10° C. for ca. 7 h. The solvent and CF3CO2H were removed under vacuum. The trace CF3CO2H was removed azeotropically with CHCl3 at the end. The residue was purified by preparative HPLC, eluting with 8% (10% conc. NH4 0H in MeOH)--CH2Cl2 to afford 3.57 g (92%) of the serinamide: mp 97-98° C.; 1H NMR (CDCl3) δ7.82 (br s, 1H), 7.26 (m, 5H), 4.42 (ddd, J=16.7, 15.0, 6.0 Hz, 2H), 3.85 (dd, J=10.8, 5.2 Hz, 1H), 3.70 (dd, J=10.8, 5.3 Hz, 1H), 3.44 (m, 1H), 2.22 (br s, 3H); FDMS 195 (M+1). Anal. (C10H14N2O2) C, H, N.

1. washwashed with 100 mL of H2O (2×) and brine (1×)
2. dry with materialThe combined organic layers were dried over MgSO4
3. concentrationconcentrated
4. customAfter drying under vacuum overnight
5. dissolutionthe residue was dissolved in 20 mL of CH2Cl2
6. additiontreated with 20 mL of CF3CO2H at 0-10° C. for ca. 7 h
7. customThe solvent and CF3CO2H were removed under vacuum
8. customThe trace CF3CO2H was removed azeotropically with CHCl3 at the end
9. customThe residue was purified by preparative HPLC
10. washeluting with 8% (10% conc. NH4 0H in MeOH)

ORD record

ord-e094cd6c2ec143d990812d7fe61f873f

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05990308