4-Methylmorpholine → HCID 66842904, compound

Participants

Reaction Steps

To a solution of N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}glycine (0.05 g, 0.092 mmol) and N-methyl morpholine (0.037 g, 0.37 mmol) in DMF (2 ml), under an atmosphere of nitrogen, was added TBTU (0.039 g, 0.12 mmol). After 1.5 h, 3-cyclopentyl-D-alanine (0.022 g, 0.139 mmol) was added. The reaction was allowed to stir for 1 h after which water (1 ml) was added. After 10 minutes, MeOH (2 ml) and NaBH4 (0.035 g, 0.925 mmol) were added. Full conversion to the corresponding alcohol was achieved within 5 minutes. The reaction was quenched by the addition of 0.1M NH4OAc buffer (2 ml) and the product was isolated by preparative HPLC of the mixture (eluent 0-50% CH3CN in 0.1M NH4OAc buffer). Freeze drying of pure fractions afforded the desired compound (0.031 g, 49%) as a colourless solid. m/z: 680.7 (M−1). 1H NMR [(CD3)2SO), 400 MHz] δ 0.97-1.10 (m, 2H), 1.38-1.81 (m, 9H), 2.84-2.94 (m, 2H), 3.77 (d, 2H), 4.11-4.16 (m, 1H), 4.25-4.28 (m, 1H), 4.51 (s, 2H), 4.69-4.75 (m, 1H), 5.03-5.06 (m, 1H), 6.97-7.37 (m, 12H), 8.02-8.06 (m, 1H), 8.22 (t, 1H).

Provenance & Evidence