Potassium Carbonate → Methyl 2-{[(4-ethoxyphenyl)sulfonyl]-4-methylanilino}propanoate

HRID 971320Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

The crude N-aryl-benzenesulfonamide building block XIII, e.g. 4-ethoxy-N-(4-methylphenyl)benzenesulfonamide (204 mg, 0.70 mmol, preparation described in example 1, step a)), was dissolved in DMF (5 mL). Methyl-2-bromopropionate (0.117 mL, 1.05 mmol) and potassium carbonate (193 mg, 1.40 mmol) were added. The mixture was heated overnight at 60° C. Solvents were evaporated. The crude residue was suspended in ethyl acetate (10 mL) and was washed with 1N HCl solution (7 mL) and with brine (7 mL). Organic phase was dried over MgSO4, fltrated and evaporated. The desired product, e.g. methyl 2-{[(4-ethoxyphenyl)sulfonyl]-4-methylanilino}propanoate (276 mg, quantitative crude yield) was isolated as a light yellow oil, in 94.3% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

customSolvents were evaporated
washwas washed with 1N HCl solution (7 mL) and with brine (7 mL)
dry with materialOrganic phase was dried over MgSO4
customevaporated

Sources & evidence

ORD record: ord-47c63fdbd517494bbc401ec578cd0e6f
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312358B2

Reaction notes

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