Water → HCID 86721879, compound

HRID 1049029Notes

Reaction equation

[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]([CH2:19][CH:20]([CH3:22])[CH3:21])[S:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.B(Cl)(Cl)Cl.O.C([O-])(O)=O.[Na+]>C(Cl)Cl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]([CH2:19][CH:20]([CH3:22])[CH3:21])[S:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of N-(4-chloro-benzyl)-N-isobutyl-4-methoxy-benzenesulfonamide (1.03 g, 2.8 mmol) in DCM (25 mL) was added tetrabutylammonium iodide (1.14 g, 3.1 mmol) and the reaction was cool to −78° C. To the solution was added boron trichloride (4.2 mL, 4.2 mmol of 1 M solution in DCM) over 2 minutes then stirred for a further 5 minutes. The reaction was left to warm to 0° C. and stirred for further 2 hours. Water and saturated aqueous NaHCO3 were added, extracted with DCM, filtered through a phase separator, concentrated then purified by silica gel column chromatography (0-30% EtOAc in cyclohexane) to give N-(4-chloro-benzyl)-4-hydroxy-N-isobutyl-benzenesulfonamide (629 mg, 64%). LCMS (m/z, Method A) ES− 352 [M−1]−.

Workup

waitThe reaction was left
temperatureto warm to 0° C.
stirringstirred for further 2 hours
extractionextracted with DCM
filtrationfiltered through a phase separator
concentrationconcentrated
customthen purified by silica gel column chromatography (0-30% EtOAc in cyclohexane)

Sources & evidence

ORD record: ord-720e82b5512a4ceaa04e1ac6b9fdd8c0
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382222B2

Reaction notes

Loading…