Picolyl chloride → HCID 19992182, compound

HRID 345303Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A stirred suspension of sodium hydride (20 mg) in dimethylsulfoxide (2 ml) was heated at 60° C. under nitrogen atmosphere. After one hour, 1-phenylmethyl-11-oxo-7-thia-10-azaspiro[5.6]dodecane 7,7-dioxide (0.20 g) and 2-pyridylmethyl chloride (0.2 ml) were added to the solution and the mixture was allowed to stand at room temperature for one hour. The mixture was diluted with ethyl acetate (20 ml) and washed with a saturated aqueous solution (20 ml) of sodium bicarbonate, water (20 ml) and brine (20 ml). The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was purified with silica gel (6 g) column chromatography (ethyl acetate) to give 1-phenylmethyl-10-(2-pyridylmethyl)-11-oxo-7-thia-10-azaspiro[5.6]dodecane 7,7-dioxide (0.21 g).

Workup

waitto stand at room temperature for one hour
washwashed with a saturated aqueous solution (20 ml) of sodium bicarbonate, water (20 ml) and brine (20 ml)
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified with silica gel (6 g) column chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-69dd9780be574bf1a8b62a945d28b455
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05057513

Reaction notes

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