Sodium Hydroxide → HCID 19747374, compound

Participants

Reaction Steps

4-(3-(Tertiarybutoxycarbonylamino)propyl)phenylacetic acid methyl ester (2.0 g) was dissolved in 50% aqueous methanol (100 ml) with sodium hydroxide (1 g) and stirred at room temperature for 14 h. The methanol was removed under vacuum and the residual aqueous solution was acidified to pH1 using 1N hydrochloric acid, and the resulting precipitate extracted into ethyl acetate (2×100 ml). The combined organic extracts were dried (Na2SO4), filtered and concentrated under vacuum to give the required product as a white solid (1.82 g). δ (360 MHz, CDCl3) 1.44 (9H, s, COC(CH3)3, 1.78 (2H, m, CH2CH2CH2NH), 2.60 (2H, t, J=7.5 Hz, CH2CH2CH2NH), 3.13 (2H, m, CH2CH2CH2NH), 3.60 (2H, s, CH2CO2H), 4.57 (1H, br, s, NH), 7.12 (2 H, d, J=8.0 Hz, ArH), 7.19 (2H, d, J=8.0 Hz, ArH); m/e (CI) 294 (M+1).

Provenance & Evidence