Chloroacetic Acid → HCID 131724484, compound

Participants

Reaction Steps

A solution of MEt-IDA-(Phe-Lys(Mtr)-PABC-MMC)2 30 (134.6 mg, 0.0590 mmol) in methylene chloride (3 mL) at rt was treated with anisole (1.28 mL, 200 equiv) and 1 M chloroacetic acid in methylene chloride (1.18 mL, 20 equiv). After 3.5 h ethyl acetate (30 mL) was added. The resulting purple solid was collected by filtration, washed with ethyl acetate and air-dried (97.8 mg, 82%). The product appeared to decompose in solution to one product by HPLC. 1H-NMR (CDCl3/CH3OD) δ 1.33 (m, 4H), 1.63 (s and M, 12H), 1.77 (m, 2H), 2.52 (m, 2H), 2.82 (m, 6H), 3.03 (m, 2H), 3.10 (s and brs, 10H), 3.27 (m, 2H), 3.53 (ABq, 2H), 3.96 (brs, 4H), 4.11 (m, 2H), 4.35 (d and m, 3H), 4.53 (m, 2H), 4.78 (ABq, 2H), 4.94 (m, 4H), 6.62 (s, 2H), 7.10 (m, 10H), 7.19 (d, 4H), 7.41 (d, 4H). MS (FAB) 1738.3 (M+Na)+, 1776.4 (M+K)+.

Provenance & Evidence