Triethylamine → p-Methoxybenzyl [3-(t-butyloxycarbonylamino)-1-propylamino]acetate

To a cold (0-5° C.) solution of 3-(t-butyloxycarbonylamino)-1-propylamine (4.00 g, 23 mmol) and triethylamine (2.8 mL, 20 mmol) in anhydrous CH2Cl2 (15 mL) was added slowly a solution of p-methoxybenzyl bromoacetate (5.18 g, 20 mmol) in anhydrous CH2Cl2 (10 mL) over a period of 2.5 h. The mixture was stirred at 0°-5° C. for 2 h, at which time TLC indicated that the reaction was complete. The mixture was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a dark residue. The crude material was purified by column chromatography on silica gel (elution with 50% ethyl acetate/hexane) to afford 2.81 g (40% yield) of p-methoxybenzyl [3-(t-butyloxycarbonylamino)-1-propylamino]acetate as an amber oil. 1H NMR (300 MHz, CDCl3 )δ1.41 (s, 9 H), 1.61 (quint, J=7 Hz, 2 H), 2.63 (t, J=7 Hz, 2 H), 3.17 (q, J=6 Hz, 2 H), 3.38 (s, 2 H), 3.78 (s, 3 H), 5.07 (s, 2 H), 6.86 (m, 2 H), and 7.26 (m, 2 H); IR (film), 1736, 1708 cm-1 ; MS (isobutane-DCI) MH+ =353. Anal. Calcd. for C18H28N2O5 : C, 61.35; H, 8.01; N, 7.95. Found: C, 60.87; H, 8.30; N, 7.89.

1. washThe mixture was washed with water and saturated sodium chloride solution
2. dry with materialdried over anhydrous sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customto give a dark residue
6. customThe crude material was purified by column chromatography on silica gel (elution with 50% ethyl acetate/hexane)

ORD record

ord-fb0a362f72b0471b8ed91b7bb24e116e

Source dataset

uspto-grants-1997_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05668290