Sodium Sulfite → HCID 11799781, compound

HRID 1885612Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([CH2:11][CH:12]([C:19](=[O:31])[N:20]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].ClC1C=CC=C(C(OO)=[O:40])C=1.S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([CH2:11][CH:12]([C:19](=[O:31])[N:20]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])(=[O:40])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 0 °C

Procedure

Into a solution of methyl 5-(3,4-dichlorophenylsulfinyl)-4-(N,N-dipentylcarbamoyl)pentanoate (95 mg) in dry dichloromethane (10 ml) were added portions of m-chloroperbenzoic acid (80%, 51 mg) with stirring at 0° C. After stirring at room temperature 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 recrystallized from hexane to give 100 mg of methyl 5-(3,4-dichlorophenylsulfonyl)-4-(N,N-dipentylcarbamoyl)pentanoate. The physical properties of this compound were identical to that of the compound which was prepared in example 1.

Workup

stirringAfter stirring at room temperature 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 recrystallized from hexane

Sources & evidence

ORD record: ord-9c4524701c354e6cb2b143547322ba53
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05145869

Reaction notes

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