Sodium Sulfite → HCID 19879354, compound

HRID 1885607Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][CH:11]([C:18](=[O:33])[N:19]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:5]=[CH:6][C:7]=1[Cl:8].ClC1C=CC=C(C(OO)=[O:42])C=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([CH2:10][CH:11]([C:18](=[O:33])[N:19]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[O:42])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: -78 °C

Procedure

Into a solution of methyl 5-(3,4-dichlorophenylthio)-4-(N-pentyl-N-phenethylcarbamoyl)pentanoate (280 mg) in dry chloroform (10 ml) were added portions of m-chloroperbenzoic acid (70%, 140 mg) with stirring at -78° C. After stirring at -78° C. for 2 hours, sodium sulfite was added. The reaction mixture was washed with a saturated sodium bicarbonate solution and water, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica by eluting with dichloromethane/diethy ether/hexane (1:1:2) to give 100 mg of methyl 5-(3,4-dichlorophenylsulfinyl)-4-(N-pentyl-N-phenethylcarbamoyl)pentanoate (diastereomer A) in a early fraction and 110 mg of diastereomer B in a later fraction.

Workup

stirringAfter stirring at -78° C. for 2 hours
washThe reaction mixture was washed with a saturated sodium bicarbonate solution and water
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica
washby eluting with dichloromethane/diethy ether/hexane (1:1:2)

Sources & evidence

ORD record: ord-85bb5ac213d84392bd26af8dc9b27aa0
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05145869

Reaction notes

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