4-Toluenesulfonyl chloride → HCID 13355956, compound

HRID 538754Notes

Reaction equation

Cl.C([N:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH:6]([C:11]([OH:13])=[O:12])[CH2:5]1)C.C(N([CH2:19][CH3:20])CC)C.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>ClCCl>[CH3:31][C:21]1[CH:26]=[CH:25][C:24]([S:27]([N:4]2[CH2:9][CH2:8][C:7](=[O:10])[CH:6]([C:11]([O:13][CH2:19][CH3:20])=[O:12])[CH2:5]2)(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

0.200 g (0.97 mmol) of 1-ethyl-4-oxopiperidine-3-carboxylate hydrochloride (commercially available, ABCR) were dissolved in 4 mL of dichloromethane with 0.135 mL (0.97 mmol) of triethylamine. The solution was cooled down to 0° C. and 0.185 g (0.97 mmol) of para-toluenesulfonyl chloride were added followed by 0.135 mL (0.97 mmol) of triethylamine. The reaction was stirred for 20 minutes at 0° C. and overnight at room temperature. Then, the reaction was further diluted with dichloromethane (50 mL) and washed with brine (20 mL×2). The organic layer was dried over Na2SO4 and solvent evaporation gave 300 mg of a white solid (95% yield) which was used for the following step without further purification.

Workup

washwashed with brine (20 mL×2)
dry with materialThe organic layer was dried over Na2SO4 and solvent evaporation

Sources & evidence

ORD record: ord-9bbeb38b65e24f93be1a339b5b5f2dfa
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865758B2

Reaction notes

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