Triethylamine → (S)-1-[2-(2-benzenesulfonyl-ethyl-BOC-amino)-acetyl]-pyrrolidine-2-carbonitrile

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Reaction Steps

[(2-benzenesulfonyl-ethyl)-BOC-amino]-acetic acid (288 mg, 0.84 mmol) and (S)-pyrrolidine-2-carbonitrile (111 mg, 0.84 mmol) were combined in CH2Cl2 (10 mL) at 0° C. EDCI (192 mg, 1.0 mmol) and triethylamine (280 μL, 2.0 mmol) were added, and the reaction stirred for 3 h while warming to r.t. The solution was washed with 0.1 N HCl and brine, dried (Na2SO4), and concentrated in vacuo. Purification by silica gel chromatography (75% EtOAc/hexanes) gave 188 mg (53%) of (S)-1-[2-(2-benzenesulfonyl-ethyl-BOC-amino)-acetyl]-pyrrolidine-2-carbonitrile as a white foam. 1H NMR (300 MHz, CDCl3): δ 7.91 (t, 2H, J=4.8 Hz), 7.54-7.69 (m, 3H), 4.69-4.79 (m, 1H), 4.17 (t, 1H, J=12.0 Hz), 3.87 (t, 1H, J=12.0 Hz), 3.40-3.77 (m, 6H), 2.12-2.32 (m, 4H), 1.39 (d, 9H, J=5.1 Hz). MS (ES) [m+H]/z calculated for C20H27N3O5S+H 422.17, found 422.10.

Provenance & Evidence