Dimethylformamide → HCID 20610693, compound

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Reaction Steps

Compound 4 (32.2 mg, 0.102 mmole) was dried overnight in vacuo (with P2O5). Dry DMF (2 mL) was added and the mixture was stirred with warming to affect dissolution under nitrogen. Triethylamine (34 mcL) was added followed by 1 (20.4 mcL, 0.115 mmole) added in two 10.2 mcL portions, 5 min apart. The mixture was stirred for 1 hr at room temperature under nitrogen. 12-Aminododecanic acid (24.1 mg, 0.112 mmole, Sigma) was added in one portion, and the mixture was stirred at room temperature for 2 hr under nitrogen. CHCl3 (80 mL) was added, and the organic solution was washed with two 10 mL portions of 1 M HCl. CHCl3 was removed by rotary evaporation, and residual DMF was removed by vacuum centrifugation. The compound was dissolved in methanol and purified by HPLC (Vydac 218TP prep column). Solvent program is: 0-10 min, water with 0.06% TFA; 10-55 min, 0-100% methanol with 0.06% TFA, flow rate is 6 mL/min. Yield 31.7 mg. 1H-NMR. ESI-MS, calculated 513.4, observed 513.4 (M+H)+

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