4-Aminobenzyl alcohol → HCID 131726473, compound

Participants

Reaction Conditions

Reaction Steps

100 mg (0.105 mmol) of Aloc-D-Ala-Phe-Lys(Aloc)-PABC-PABC-PNP 18 was dissolved in dry N,N-diethylformamide under an argon atmosphere and cooled to −8° C. 4-Aminobenzylalcohol (14.2 mg, 1.1 equiv), dipea (18.3 μl, 1.0 equiv) and 1-hydroxybenzotriazole (HOBt) (4 mg, 0.3 equiv) were added. The reaction mixture was stirred for 48 hours at room temperature, and diluted with 10% 2-propanol/ethyl acetate. The organic layer was washed with water, saturated sodium bicarbonate, 0.5 N potassium bisulfate, and brine, dried over sodium sulfate (Na2SO4), and evaporated to yield the desired product 34 as a cream colored powder 86 mg (88%). 1H NMR (300 MHz CDCl3) δ 0.95–2.05 (m, 9H, 3CH2-Lys and CH3-Ala), 2.88–3.11 (m, 4H, 2H Bn-Phe and N—CH2-Lys), 3.95–4.62 (m, 7H, 3Hα and 4H Aloc), 4.75 (s, 2H, CH2—OH), 5.12–5.21 (m, 6H, 4 Aloc and CH2-Bn), 5.09 (s, 2H, CH2-Bn), 5.65–6.00 (m, 2H, Aloc), 6.79–7.41 (m, 15H, aromatic) 7.62 (d, 2H, aromatic) ppm; MS (FAB) m/e 959 (M+Na)+.

Provenance & Evidence