Benzenesulfonyl chloride → HCID 18449980, compound

HRID 1270485Notes

Reaction equation

[CH:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[CH2:14][CH2:15][C:16]([OH:18])=[O:17])([CH3:3])[CH3:2].C([Li])CCC.[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1.C(OCC)(=O)C.Cl>[CH:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([S:30]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:32])=[O:31])[CH:9]=[C:8]2[CH2:14][CH2:15][C:16]([OH:18])=[O:17])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

To a cooled (−78° C.) solution of propionic acid (27) (96.3 mg, 0.510 mmol) in tetrahydrofuran (10 ml), n-butyl lithium (1.40 ml, 2.24 mol) was added next and stirred for 30 minutes at −78° C. Benzene sulfonyl chloride (277 mg, 1.5 mmol) was added next, and the reaction was stirred for 16–24 hours, allowing temperature to rise from −78° C. to ambient conditions. The reaction was then diluted with ethyl acetate, and 1M HCl was added to adjust the pH to 1–2. The layers were then separated, and the organic layer was placed over magnesium sulfate and concentrated under reduced pressure. The crude material was then purified by flash chromatography with silica, eluting with 5% methanol in dichloromethane to yield the desire product (22) as a white solid. (M−1=386.4)

Workup

additionwas added next
stirringthe reaction was stirred for 16–24 hours
customto rise from −78° C. to ambient conditions
additionwas added
customThe layers were then separated
concentrationconcentrated under reduced pressure
customThe crude material was then purified by flash chromatography with silica
washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record: ord-07e7dcc9a798488ea92da2521b802bc3
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202266B2

Reaction notes

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