Benzylamine → N-Benzyl-[4-(4-methoxyphenylthio)-2-oxoazetidin-1-yl]acetamide

HRID 1603670Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH:10]2[N:13]([CH2:14][C:15]([OH:17])=O)[C:12](=[O:18])[CH2:11]2)=[CH:5][CH:4]=1.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([NH:26][C:15](=[O:17])[CH2:14][N:13]1[CH:10]([S:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:11][C:12]1=[O:18])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Reactant 2

HCID 7504Benzylamine

HCID 19605269(4-(4-Methoxyphenylthio)-2-oxoazetidin-1-yl)acetic acid

Product 1

HCID 19605397N-Benzyl-[4-(4-methoxyphenylthio)-2-oxoazetidin-1-yl]acetamideYield 74%

Procedure

Treatment of (4-(4-methoxyphenylthio)-2-oxoazetidin-1yl)acetic acid with benzylamine under the conditions described in Example 86 gave the title compound as a colourless oil, 74% yield. 1H NMR δ (CDCl3) 2.80, 2.86 (1H, dd, J=2.3, 15.2 Hz, H3), 3.29, 3.35 (1H, dd, J=5, 15.2 Hz, H3), 3.79 (3H, s, OCH3), 3.85, 4.05 (each 1H, d, J=16.7 Hz, NCH2), 4.43 (2H, d, J=5.7 Hz, NHCH2), 4.97 (1H, m, H4) 6.5 (1H, m, NH), 6.83 (2H, d, J=8.6 Hz, 4-OCH3Ph-H), 7.24-7.35 (7H, m, Ph-H, 4-OCH3Ph-H). ν c=o 1775 cm-1. Found: C, 64.0 H, 5.8; N, 8.1%. C19H20N2O3S requires: C, 64.0; H, 5.7 N, 7.9%

Sources & evidence

ORD record: ord-ec765e42446b43df939d559f13c8cee3
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990102

Reaction notes

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