Diisopropylethylamine → HCID 67273951, compound

Participants

Reaction Steps

To a solution of (3S,5R)-3-Amino-5-{cyclopropyl-[4-(3-methoxy-propyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-carbamoyl}-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester hydrochloride salt (100 mg, 0.152 mmol) and 1-Cyano-cyclo-propanecarboxylic acid (20 mg, 0.182 mmol) in DMF (10 mL) is added EDC-HCl (45 mg, 0.227 mmol), HOAt (31 mg, 0.227 mmol) and diisopropylethylamine (0.04 mL, 0.227 mmol) at 0° C. The mixture is stirred for 14 h at r.t. and diluted with ethyl acetate, and washed with H2O. The organic layer is dried over MgSO4 and evaporated in vacuo. The residue is purified by silica-gel column chromatography to afford the title compound as a white solid. MS: 746 [M+H]+; tR (CombiScreen ODS-AM, 50×4.6 mm; 5% CH3CN+0.1% TFA/H2O+0.1% TFA for 0.5 min then 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 5 min then 100% CH3CN+0.1% TFA for 2 min, flow 2.0 ml/min): 2.14 min.

Provenance & Evidence