Potassium Iodide → Boc methylenedioxybenzenesulfonamide 3-methyl-5-methylisoxazole

HRID 1815538Notes

Reaction equation

C([CH:8]1[O:16][C:15]2[C:10](=[C:11]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:12]=[CH:13][CH:14]=2)[O:9]1)(OC(C)(C)C)=O.[C:21](=[O:24])([O-])[O-:22].[Cs+].[Cs+].Cl[CH2:28][C:29]1[CH:33]=[C:32]([CH3:34])[O:31][N:30]=1.[I-].[K+].O1CCOC[CH2:38]1>C(OCC)(=O)C.CCCCCC>[CH3:28][C:29]1[CH:33]=[C:32]([CH3:34])[O:31][N:30]=1.[CH2:8]1[O:16][C:15]2[C:10](=[C:11]([S:17]([NH:20][C:21]([O:22][C:32]([CH3:33])([CH3:34])[CH3:38])=[O:24])(=[O:18])=[O:19])[CH:12]=[CH:13][CH:14]=2)[O:9]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of Boc methylenedioxybenzenesulfonamide free phenol (0.010 g, 0.020 mmol) in 1,4-dioxane (1 mL) was combined with cesium carbonate (0.015 g, 0.047 mmol), 3-chloromethyl-5-methyl isoxazole (0.004 g, 0.028 mmol) and potassium iodide (˜1 mg, 0.006 mmol). The solution was heated to 60° C. with stirring for 16 hours, and was cooled and dried in vacuo to give a pale yellow oil. Flash column chromatography (3:7 ethyl acetate/hexane) gave Boc methylenedioxybenzenesulfonamide 3-methyl-5-methylisoxazole tethered product (0.005 g, 42%) as a colourless oil: Rf=0.25 (3:7 ethyl acetate/hexane); 1H NMR (CDCl3) 7.34 (1H, dd, J=8.4, 1.8 Hz), 7.21-7.13 (3H, m), 6.90 (3H, m), 6.11 (1H, s), 6.09 (2H, s), 5.09 (2H, s), 4.65 (1H, d, J=8.2 Hz), 3.92 (1H, br. s), 3.82-3.75 (1H, m), 3.73-3.63 (1H, m), 3.09-3.03 (2H, m), 2.98-2.80 (4H, m), 2.43 (3H, s), 1.84 (1H, septet, J=6.6 Hz), 1.36 (9H, s), 0.91 (3H, d, J=6.6 Hz), 0.88 (3H, d, J=6.6 Hz).

Workup

temperaturewas cooled
customdried in vacuo
customto give a pale yellow oil

Sources & evidence

ORD record: ord-c49ec3f2618c4c5882d3c09868e8fb22
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06878728B1

Reaction notes

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