p-Toluenesulfonic acid → N-(6-(2,4-Difluorophenyl)hexyl)-(4-benzylthio-2-oxoazetidin-1-yl)acetamide

HRID 1603658Notes

Reaction equation

HRID 1603658 reaction equation
[CH2:1]([S:8][CH:9]1[N:12]([CH2:13][C:14]([OH:16])=O)[C:11](=[O:17])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[F:29][C:30]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=1[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][NH2:43]>CN(C)C=O>[F:29][C:30]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=1[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][NH:43][C:14](=[O:16])[CH2:13][N:12]1[CH:9]([S:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:10][C:11]1=[O:17]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 19605256(4-Benzylthio-2-oxoazetidin-1-yl)acetic acidHCID 196054086-(2,4-Difluorophenyl)hexylamine

Product 1

HCID 19605334N-(6-(2,4-Difluorophenyl)hexyl)-(4-benzylthio-2-oxoazetidin-1-yl)acetamideYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sequential treatment of (4-benzylthio-2-oxoazetidin-1-yl)acetic acid with 1-cyclohexyl-3-(2-morpholinethyl)carbodiimide metho-p-toluenesulfonate and 6-(2,4-difluorophenyl)hexylamine in dimethyl formamide by the method described for Example 29 gave the title compound as a colourless solid, m.p. 65-66° C., in 73% yield 1H NMR δ (CDCl3) 1.3-1.36 (4H, m, 4×CH2), 1.50-1.60 (4H, m, 4×CH2), 2.58 (2H, t, J=7.6 Hz, PhCH2), 2.93, 2.97 (1H, dd, J=2.4, 15.6 Hz, H3), 3.23 (2H, m, NHCH2), 3.35, 3.39 (1H, dd, J=5.2, 15.2 Hz, H3), 3.57, 3.71 (each 1H, d, J=16.4 Hz, NCH2), 3.81 (2H, s, SOCH2), 4.80 (1H, m, H4), 6.02 (1H, m, HH), 6.76-7.33 (8H, m, 2Ph--H); νc=o 1774 cm-1Found: C, 64.5; H, 6.3; N, 6.5%, C24H28F2N2O2S requires: C, 64.6; H, 6.3; N, 6.3%

Sources & evidence

ORD record
ord-e211b40520bf4169bd0c0f280ee84877
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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