3-(Methoxycarbonyl)benzeneboronic acid → HCID 67139600, compound

HRID 1592014Notes

Reaction equation

HRID 1592014 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[C:10](=[O:11])[CH2:9][NH:8][S:7]1(=[O:13])=[O:12].[CH3:20][O:21][C:22]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)=[O:23]>O1CCOCC1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:20][O:21][C:22](=[O:23])[C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([N:8]2[CH2:9][C:10](=[O:11])[N:6]([CH2:5][C:4]3[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:3]=3[O:2][CH3:1])[S:7]2(=[O:13])=[O:12])[CH:29]=1

Participants

5

Reactant 2

HCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 66751042HCID 66751042, compound

Product 1

HCID 67139600HCID 67139600, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of the title B compound in Example 36, 2-(2,4-dimethoxybenzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (115 mg, 4.02 mmol) and 3-methoxycarbonyl phenylboronic acid (145 mg, 8.04 mmol) in 1,4-dioxane (5 mL) is treated with copper(II) acetate (110 mg, 6.03 mmol) and CS2CO3 (262 mg, 8.04 mmol). The mixture is stirred at RT for 16 h and the solvent is evaporated. The residue is partitioned between EtOAc and 1N aqueous HCl. The organic layer is dried over anhydrous Na2SO4 and concentrated. The residue is flash chromatographed on silica gel using 30% EtOAc in hexanes as the eluent to give 3-[5-(2,4-dimethoxybenzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]benzoic acid methyl ester as a clear oil: [M+NH4]+=438.

Workup

  1. customthe solvent is evaporated
  2. customThe residue is partitioned between EtOAc and 1N aqueous HCl
  3. dry with materialThe organic layer is dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customchromatographed on silica gel using 30% EtOAc in hexanes as the eluent

Sources & evidence

ORD record
ord-c5bb58f8a4fb4264919b5c8c1edeb024
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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