3-Nitro-2-pyridinesulfenyl → tert-Butyl (4-{(2R,3R)-1-(4-chlorophenyl)-3-[(3-nitropyridin-2-yl)dithio]-4-oxoazetidin-2-yl}phenoxy)acetate

HRID 603925Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13]CC3C=CC(OC)=CC=3)[C@H:9]2[C:23]2[CH:37]=[CH:36][C:26]([O:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:25][CH:24]=2)=[CH:4][CH:3]=1.[N+:38]([C:41]1[C:42]([S:47]Cl)=[N:43][CH:44]=[CH:45][CH:46]=1)([O-:40])=[O:39]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13][S:47][C:42]3[C:41]([N+:38]([O-:40])=[O:39])=[CH:46][CH:45]=[CH:44][N:43]=3)[C@H:9]2[C:23]2[CH:24]=[CH:25][C:26]([O:27][CH2:28][C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])=[CH:36][CH:37]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

tert-Butyl (4-{(2R,3R)-1-(4-chlorophenyl)-3-[(4-methoxybenzyl)thio]-4-oxoazetidin-2-yl}phenoxy)acetate (Method 26) (0.9 g, 1.7 mmol) was dissolved in CH2Cl2 (50 mL) and given 0° C. under inert atmosphere. 3-Nitro-2-pyridinesulfenyl chloride (0.4 g, 2.0 mmol) was added and the mixture was stirred for 30 minutes at 0° C., then 30 minutes at room temperature. Concentration under reduced pressure and purification by flash-chromatography (Heptane:EtOAc 3:1 then 2:1) afforded the title compound.

Workup

customgiven 0° C. under inert atmosphere
custom30 minutes
customat room temperature
concentrationConcentration
customunder reduced pressure and purification by flash-chromatography (Heptane:EtOAc 3:1

Sources & evidence

ORD record: ord-95f8e9bde5f64a74806b22a189e6a725
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906502B2

Reaction notes

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