3-Methylbenzenesulphonyl chloride → 3-(3-Methylphenylsulfonyl)amino-6-isopropyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

HRID 749092Notes

Reaction equation

[NH2:1][C:2]1[C:3](=[O:19])[N:4]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:5]([CH:8]([CH3:10])[CH3:9])=[CH:6][CH:7]=1.[C:20]1([CH3:30])[CH:25]=[CH:24][CH:23]=[C:22]([S:26](Cl)(=[O:28])=[O:27])[CH:21]=1>C(Cl)Cl>[CH3:30][C:20]1[CH:21]=[C:22]([S:26]([NH:1][C:2]2[C:3](=[O:19])[N:4]([CH2:11][C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[C:5]([CH:8]([CH3:9])[CH3:10])=[CH:6][CH:7]=2)(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-Amino-6 isopropyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone (assumed to be 3.37 mmol), as prepared in the preceding step, and N-methylmbrpholine (1.0 mL, 9.1 mmol) were dissolved in methylene chloride (20 mL) and cooled to 0° C. A solution of m-toluenesulfonyl chloride (0.67 g, 3.5 mmol) in methylene chloride (5 mL) was added and the reaction stirred at ambient temperature for 16 hours. After evaporation in vacuo, the crude product was dissolved in methylene chloride, washed with 10% aqueous citric acid, saturated NaHCO3, and brine, dried over MgSO4, and filtered. The evaporated filtrate gave the title compound (1.24 g, 88%) as a tan solid. 1H NMR (300 MHz, CDCl3) δ 7.65 (m, 2H), 7.58 (br s, 1H), 7.46 (d, 1H, J=7.8 Hz), 7.33 (m, 2H), 6.08 (d, 1H, J=7.9 Hz), 4.69 (s, 2H), 2.67 (m, 1H), 2.38 (s, 3H), 1.41 (s, 9H), 1.22 (s, 3H), 1.19 (s, 3H).

Workup

customAfter evaporation in vacuo
dissolutionthe crude product was dissolved in methylene chloride
washwashed with 10% aqueous citric acid, saturated NaHCO3, and brine
dry with materialdried over MgSO4
filtrationfiltered

Sources & evidence

ORD record: ord-37303db64eeb412b825e79856a9010da
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402586B2

Reaction notes

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