4-(Methylsulfanyl)azetidin-2-one → HCID 20336556, compound

HRID 1706129Notes

Reaction equation

HRID 1706129 reaction equation
[CH3:1][S:2][CH:3]1[NH:6][C:5](=[O:7])[CH2:4]1.Br[CH2:9][C:10](=[O:18])[CH2:11][C:12](=[O:17])[C:13]([O:15][CH3:16])=[O:14]>>[CH3:1][S:2][CH:3]1[N:6]([CH2:9][C:10](=[O:18])[CH2:11][C:12](=[O:17])[C:13]([O:15][CH3:16])=[O:14])[C:5](=[O:7])[CH2:4]1

Participants

3

Reactant 2

HCID 126772484-(Methylsulfanyl)azetidin-2-oneHCID 20336572HCID 20336572, compound

Product 1

HCID 20336556HCID 20336556, compound

Procedure

4-Methylthioazetidin-2-one (940 mg., 8 mmole) and methyl 5-bromo-2,4-dioxopentanoate (2.21 g., 10 mmole) were converted into the title compound using the process described in Example 24.1. The title compound was obtained as a pale yellow gum (550 mg., 27% yield). (Found: M+, 259.05113. C10H13NO5S requires 259.05144). νmax (CHCl3): 1750 (br.) (β-lactam and ester C=O), 1650 and 1600 (β-diketone C=O) cm-1. δ(CDCl3): 2.00 (s, 3H, SCH3), 2.98 (dd, J 16 J' 2 Hz, 1H, β-lactam CHH), 3.43 (dd, J 16, J' 5 Hz, 1H, β-lactam CHH), 3.80 (s, 3H, OCH3), 3.80 (d, J 17 Hz, 1H, NCHH), 4.31 (d, J 17 Hz, 1H, NCHH), 4.73 (dd, J 5, J' 2 Hz, 1H, β-lactam CH), 6.46 (s, 1H, enol, olefinic H), 11.8 (br.s, 1H, enol, OH). m/3: 259 (M+ 9%), 212 (100), 184 (8), 170 (19), 155 (28), 152 (40), 116 (80), 110 (95).

Sources & evidence

ORD record
ord-13bda557f6684d518f9328b95865c547
Source dataset
uspto-grants-1980_06
Patent number
US04206120

Reaction notes

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