Yield:133264-58-1 83%

Reaction Conditions:

with triethylamine in dichloromethane at -78 - 20;

Steps:

General procedure for synthesis of 2-chloroacetamide derivatives (5a-j) from mono-Boc protected diamines (2a-j)

General procedure: A solution of the corresponding mono-Boc-protected diamine 2a-j (1.0 equiv.) in CH2Cl2 (0.5 M) was cooled to -78 C (acetone/dry ice). NEt3 (1.5 equiv.) was rapidly added before a solution of chloroacetyl chloride (1.2 equiv.) in CH2Cl2 (0.5 M) was added dropwise for 30-60 min. The resulting white slurry mixture was left to warm up to room temperature to become dark brown, and then was stirred at room temperature for 24 h. The resulting mixture was washed with 0.5M citric acid (3 times) and then with water (twice). The organic layer was extracted, dried over K2CO3 and the solvent removed under reduced pressure to give the title compound as a dark brown oil.

References:

Prandina, Anthony;Radix, Sylvie;Le Borgne, Marc;Jordheim, Lars Petter;Bousfiha, Zineb;Fr?hlich, Christopher;Leiros, Hanna-Kirsti S.;Samuelsen, ?rjan;Fr?vold, Espen;Rongved, P?l;?strand, Ove Alexander H?gmoen [Tetrahedron,2019,vol. 75,# 11,p. 1525 - 1540]