4-(Methylsulfanyl)azetidin-2-one → HCID 20336606, compound
Reaction equation
[CH3:1][S:2][CH:3]1[NH:6][C:5](=[O:7])[CH2:4]1.Br[CH2:9][C:10]#[C:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[O:19])=[CH:14][CH:13]=1>>[CH3:1][S:2][CH:3]1[N:6]([CH2:9][C:10]#[C:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)=[O:19])=[CH:16][CH:17]=2)[C:5](=[O:7])[CH2:4]1Participants
3
Procedure
4-Methylthioazetidin-2-one (470 mg., 4 mmole) and 3-bromo-1-[p-(p-methoxybenzyloxycarbonyl)-phenyl]-prop-1-yne (1.44 g., 4 mmole) were converted into the title compound using the process described in Example 22.1. The title compound was obtained as a colourless gum (410 mg., 27% yield). νmax (CHCl3): 1760 (β-lactam C=O), 1720 (ester C=O), 1610 and 1515 (aromatic C=C) cm-1. δ(CDCl3): 2.10 (s, 3H, SCH3), 2.91 (dd, J 15.5, J' 2 Hz, 1H, β-lactam CHH), 3.34 (dd, J 15.5, J' 5 Hz, 1H, β-lactam CHH), 3.72 (s, 3H, OCH3), 3.92 (d, J 17 Hz, 1H, NCHH), 4.40 (d, J 17 Hz, 1H, NCHH), 4.72 (dd, J 5, J' 2 Hz, 1H, β-lactam CH), 5.35 (s, 2H, OCH2Ar), 6.93 (d, J 8 Hz, 2H, Ar-H), 7.42 (d, J 8 Hz, 2H, Ar-H), 7.48 (d, J 8.5 Hz, 2H, Ar-H), 8.03 (d, J 8.5 Hz, 1H, Ar-H).