4-(Methylsulfanyl)azetidin-2-one → HCID 20336622, compound

HRID 1706128Notes

Reaction equation

HRID 1706128 reaction equation
[CH3:1][S:2][CH:3]1[NH:6][C:5](=[O:7])[CH2:4]1.Br[CH2:9][C:10](=[O:15])[CH2:11][C:12](=[O:14])[CH3:13]>>[CH3:1][S:2][CH:3]1[N:6]([CH2:9][C:10](=[O:15])[CH2:11][C:12](=[O:14])[CH3:13])[C:5](=[O:7])[CH2:4]1

Participants

3

Reactant 2

HCID 126772484-(Methylsulfanyl)azetidin-2-oneHCID 13331980HCID 13331980, compound

Product 1

HCID 20336622HCID 20336622, compound

Procedure

4-Methylthioazetidin-2-one (6.66 g., 57 mmole) and 1-bromopentan-2,4-dione (11.25 g., 63 mmole) were converted into the title compound using the process described in Example 1.1. The title compound was obtained as a colourless gum (3.13 g., 25% yield). νmax (CHCl3): 3400 (br.) (enol OH), 1760 (β-lactam C=O), 1720 (sh.) (ketone C=O), 1630 (sh.) and 1605 (enolic β-diketone C=O) cm-1. δ(CDCl3): 2.03 (s, 6H, COCH3 and SCH3), 2.97 (dd, J 16, J' 2 Hz, 1H, β-lactam CHH), 3.41 (dd, J 16, J' 5 Hz, 1H, β-lactam CHH), 3.60 (s, 0.4H, COCH2CO), 3.65 (d, J 17 Hz, 1H, NCHH), 4.18 (d, J 17 Hz, 1H, NCHH), 4.78 (dd, J 5, J' 2 Hz, 1H, β-lactam CH), 5.68 (s, 0.8H, olefinic H for enol), ca 14(v.broad, 0.8H, enolOH).

Sources & evidence

ORD record
ord-313aac60024a4af88a9d976d5befac97
Source dataset
uspto-grants-1980_06
Patent number
US04206120

Reaction notes

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