Sodium Sulfite → HCID 19879340, compound

HRID 1885618Notes

Reaction equation

[CH2:1]([N:6]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:7]([CH:9]([CH2:16][S:17]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)=[O:18])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5].ClC1C=CC=C(C(OO)=[O:39])C=1.S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[CH2:26]([N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:7]([CH:9]([CH2:16][S:17]([C:19]1[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=1)(=[O:39])=[O:18])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:8])[CH2:27][CH2:28][CH2:29][CH3:30]

Participants

Conditions

Temperature: 0 °C

Procedure

Into a solution of methyl 4-(N,N-dipentylcarbamoyl)-5-(4-methylphenylsulfinyl)pentanoate (0.15 g) in dry dichloromethane (5 ml) were added portions of m-chloroperbenzoic acid (80%, 0.09 g) with stirring at 0° C. After stirring at room temperature for 4 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/diethyl ether (2:1) to give 0.13 g of methyl 4-(N,N-dipentylcarbamoyl)-5-(4-methylphenylsulfonyl)pentanoate as an oil.

Workup

stirringAfter stirring at room temperature for 4 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/diethyl ether (2:1)

Sources & evidence

ORD record: ord-65706a278f084e8b84037ec51692b4cb
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05145869

Reaction notes

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