Sodium Sulfite → HCID 19879346, compound

HRID 1885615Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([CH2:11][CH:12]([C:19](=[O:39])[N:20]([CH2:30][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[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:48])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:39])[N:20]([CH2:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:30][CH2:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])(=[O:48])=[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-bis(3-phenylpropyl)carbamoyl]pentanoate (220 mg) in dry dichloromethane (20 ml) were added portions of m-chloroperbenzoic acid (80%, 120 mg) 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 chloroform/ethanol (50:1) to give 200 mg of methyl 5-(3,4-dichlorophenylsulfonyl)-4-[N,N-bis(3-phenylpropyl)carbamoyl]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 chloroform/ethanol (50:1)

Sources & evidence

ORD record: ord-1be0840f267843809588ca2e96809a16
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05145869

Reaction notes

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