Sodium Nitrate → cis-[(Methylethyl)sulfonyl][2-(4-nitrophenyl)cyclopentyl]amine
Reaction equation
[C:1]1([C@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[NH:12][S:13]([CH:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:19]([O-])([O-:21])=[O:20].[Na+]>FC(F)(F)C(O)=O.C(Cl)Cl>[N+:19]([C:4]1[CH:3]=[CH:2][C:1]([C@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[NH:12][S:13]([CH:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])=[CH:6][CH:5]=1)([O-:21])=[O:20]Participants
Procedure
(+,−) Cis-propane-2-sulfonic acid (2-phenyl-cyclopentyl)-amide (560 mg, 2.1 mmol, prepared in example 16) was dissolved in 10 mL of trifluoroacetic acid and 534 mg (6.3 mmol) of sodium nitrate was added. The reaction was stirred 5 hours at room temperature. The reaction was diluted with methylene chloride and washed with water and dilute sodium bicarbonate. The organic layer was dried over sodium sulfate and concentrated in vacuo to 620 mg of a crude yellow oil. This oil was purified by radial chromatography eluting with 98:2 methylene chloride:ethyl acetate to give 120 mg (18%) of the title compound as a white solid and also 400 mg (62%) which contained a small amount of ortho nitrated product. The NMR was consistent with the assigned structure.
Workup
- washwashed with water and dilute sodium bicarbonate
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated in vacuo to 620 mg of a crude yellow oil
- customThis oil was purified by radial chromatography
- washeluting with 98:2 methylene chloride
Sources & evidence
- ORD record
- ord-60788a392040441fb12eb6670a9948c5
- Source dataset
- uspto-grants-2003_10
- Patent number
- US06639107B1
Reaction notes
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