Dicyclohexylcarbodiimide → HCID 86666534, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of acid 58 (887 mg, 2.20 mmol) in dry MeCN (11 mL) at 0° C. was added N-hydroxysuccinimide (278 mg, 2.42 mmol) and DCC (499 mg, 2.42 mmol). After stirring for 4.5 h at 0° C., the reaction mixture was filtered, solids were washed with several small portions of MeCN and the combined filtrates were concentrated to dryness. The crude product was purified by flash chromatography on a Biotage™ flash chromatography system, using a gradient of 60-75% EtOAc in CH2Cl2 as eluent. Evaporation of pure fractions yielded compound 59 (744 mg, 68%) as a white foam. 1H NMR (400 MHz, CDCl3) δ 1.35-1.53 (m, 3H), 1.44 (s, 18H), 1.61-1.71 (m, 2H), 1.83-1.92 (m, 1H), 2.85 (s, 4H), 3.07-3.13 (m, 2H), 4.10-4.15 (m, 1H), 4.40 (d, J=5.7 Hz, 2H), 4.62 (bs, 1H), 5.16 (bs, 1H), 6.86 (bs, 1H).

Provenance & Evidence