Pyridine → (3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-{2-(p-toluenesulfonyl)oxy-1-phenylethoxy}-azetidin-2-one

HRID 1075648Notes

Reaction equation

[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:12]1([CH2:18][CH2:19][C:20]([NH:22][C@H:23]([C:31]([NH:33][C@H:34]2[C@@H:37]([O:38][CH:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:40][OH:41])[NH:36][C:35]2=[O:48])=[O:32])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1>ClCCl>[C:12]1([CH2:18][CH2:19][C:20]([NH:22][C@H:23]([C:31]([NH:33][C@H:34]2[C@@H:37]([O:38][CH:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:40][O:41][S:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=3)(=[O:9])=[O:8])[NH:36][C:35]2=[O:48])=[O:32])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

p-Toluenesulfonyl chloride (119 mg, 0.62 mmol) was added to an ice-cooled solution of (3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-(2-hydroxy-1-phenylethoxy)-azetidin-2-one (260 mg, 0.52 mmol) and pyridine (493 mg, 6.2 mmol) in dichloromethane (7 ml). The mixture was stirred at 0° C. for 2 hrs and then at room temperature overnight. After removal of solvent, the residue was purified by silica gel column chromatography using ethyl acetate-hexane (8:3) as eluent and 160 mg of (3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-{2-(p-toluenesulfonyl)oxy-1-phenylethoxy}-azetidin-2-one was obtained (47% yield).

Workup

customat room temperature
customovernight
customAfter removal of solvent
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-e73eea26dc414051905810556af8c7e5
Source dataset: uspto-grants-1999_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05905076

Reaction notes

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