text.skipToContent text.skipToNavigation

Maximum quantity allowed is 999

Please select the quantity

TCI Practical Example: Esterification Using N,N-DMF Di-tert-Butyl Acetal

We are proud to present the tert-butyl esterification of N-acetyl-L-phenylalanine using N,N-DMF di-tert-butyl acetal.

TCI Practical Example: Esterification Using N,N-DMF Di-tert-Butyl Acetal

Used Chemicals

Procedure

A solution of N-acetyl-L-phenylalanine (1.0 g, 4.78 mmol) in N,N-DMF di-tert-butyl acetal (6.9 mL, 28.7 mmol, 6.0 eq.) was stirred at 60 °C for overnight. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:hexane = 1:1) to give tert-butyl N-acetyl-L-phenylalaninate as a colorless oil (1.20 g, 94% yield).

Experimenter’s Comments

The reaction mixture was monitored by UPLC.

Analytical Data

tert-Butyl N-Acetyl-L-phenylalaninate

1H NMR (400 MHz, CDCl3); δ 7.28–7.19 (m, 3H), 7.13-7.11 (m, 2H), 5.92 (brd, 1H, J = 7.6 Hz), 4.76–4.71 (m, 1H), 3.07 (d, 2H, J = 6.0 Hz), 1.96 (s, 3H), 1.38 (s, 9H).

Lead Reference

Session Status
Your session will timeout in 10 minutes. You will be redirected to the HOME page after session timeout. Please click the button to continue session from the same page. minute. You will be redirected to the HOME page after session timeout. Please click the button to continue session from the same page.

Your session has timed out. You will be redirected to the HOME page.