Sodium Methoxide → Methyl 3-bromo-4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)benzoate

HRID 724678Notes

Reaction equation

HRID 724678 reaction equation
[NH2:1][S:2]([CH:5]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=1[Br:21])[CH2:6][C:7](OC)=[O:8])(=[O:4])=[O:3].C[O-].[Na+]>CO>[Br:21][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][C:11]=1[CH:5]1[S:2](=[O:4])(=[O:3])[NH:1][C:7](=[O:8])[CH2:6]1)[C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 21878646Methyl 4-[1-(aminosulfonyl)-3-methoxy-3-oxopropyl]-3-bromobenzoate

Product 1

HCID 57354419Methyl 3-bromo-4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)benzoateYield 38.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-[1-(aminosulfonyl)-3-methoxy-3-oxopropyl]-3-bromobenzoate (187 mg, 0.492 mmol) in methanol (16 mL) was treated with sodium methoxide (281 μL, 4.92 mmol) at 0° C. The solution stirred at room temperature for 3 h and 30 minutes. The reaction mixture was purified by preparative LCMS to afford product as a white solid (66 mg, 38%). 1H NMR (400 MHz, CD3OD): δ 8.31 (d, J=1.8 Hz, 1H), 8.07 (dd, J=8.2, 1.8 Hz, 1H), 7.67 (d, J=8.2 Hz, 1H), 5.71 (dd, J=8.7, 6.7 Hz, 1H), 3.94 (s, 3H), 3.52 (dd, J=17.5, 8.6 Hz, 1H), 3.27 (m, 1H). LCMS found for C11H10BrNO5SNa (M+Na)30: m/z=370, 372.

Workup

  1. customThe reaction mixture was purified by preparative LCMS

Sources & evidence

ORD record
ord-096f821b31704b3389f4ec8ef08dbfad
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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