Methylamine → HCID 10287278, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of methyl (5R)-3-[3,5-difluoro-4-(1-methoxycarbonyl-3-methylazetidin-3-yl]-2-oxo-5-oxazolidinecarboxylate (EXAMPLE 57, Step 4, 500 mg, 1.30 mmol) in MeOH (10 mL) is heated at 50° C. to achieve full dissolution, then cooled to 0° C. and treated with methylamine (15 mL, 2.0 M in MeOH). The reaction mixture is stirred for 20 min at 0° C. and then concentrated under reduced pressure. Trituration (Et2O) affords the title compound as a white solid in 90% yield; 1H NMR (400 MHz, DMSO-d6) δ 8.41 (d, 1 H), 7.35 (d, 2 H), 5.09 (dd, 1 H), 4.26 (m, 2 H), 4.25 (t, 1 H), 4.02 (dd, 1 H), 3.86 (d, 2 H), 3.56 (s, 3 H), 2.66 (d, 3 H), 1.56 (s, 3H); hMS (ESI) calcd for C17H19F2N3O5+H1 384.1371, found 384.1360; [α]25D=−35 (c 0.90, DMSO).

Provenance & Evidence