Sodium Sulfite → HCID 19879349, compound

HRID 1885610Notes

Reaction equation

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

Participants

Conditions

Temperature: -78 °C

Procedure

Into a solution of methyl 5-(3,4-dimethylphenylthio)-4-(N,N-dipentylcarbamoyl)pentanoate (0.55 g) in dry dichloromethane (10 ml) were added portions of m-chloroperbenzoic acid (70%, 0.31 g) with stirring at -78° C. After stirring at -78° C. for 3 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 benzene/ethyl acetate (2:1) to give 0.12 g of methyl 5-(3,4-dimethylphenylsulfinyl)-4-(N,N-dipentylcarbamoyl)pentanoate (diastereomer A) in a early fraction and 0.36 g of diastereomer B in a later fraction.

Workup

stirringAfter stirring at -78° C. for 3 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 benzene/ethyl acetate (2:1)

Sources & evidence

ORD record: ord-3a1158e8d52c48389ff1a735b8896ac2
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05145869

Reaction notes

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