Sulfamic Acid → Furan-2,5-dicarboxylic Acid Monobenzyl Ester

HRID 34098

Reaction equation

[CH2:1]([O:8][C:9]([C:11]1[O:12][C:13]([CH:16]=[O:17])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)([OH:20])N.Cl([O-])=O.[Na+].P([O-])(O)(O)=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.O>[CH2:1]([O:8][C:9]([C:11]1[O:12][C:13]([C:16]([OH:20])=[O:17])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

490 mg of 5-formylfuran-2-carboxylic acid benzyl ester was dissolved in 10 mL of acetonitrile, and added with a solution containing 413 mg of sulfamic acid in 5 mL of water. After cooling to 0° C., a solution containing 202 mg of sodium chlorite and 232 mg of potassium dihydrogen phosphate in 5 mL of water was added dropwise. After cooling at this temperature for 30 minutes, sodium thiosulfate aqueous solution was added at 0° C. to stop the reaction, and extracted with a mixture of tetrahydrofuran and ethyl acetate. The organic phase was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off to afford 520 mg of the title compound as white crystals.

Workup

additionadded with a solution
additionwas added dropwise
temperatureAfter cooling at this temperature for 30 minutes
customthe reaction
extractionextracted with a mixture of tetrahydrofuran and ethyl acetate
washThe organic phase was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
distillationThe solvent was distilled off

Sources & evidence

ORD record: ord-c6f74879b55d4a9f9448b3912936560b
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429609B2

Linked notes

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