Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | 5-(Hydroxymethyl)furfural | HCID 237332 | — |
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | ((2-Thienylcarbonyl)amino)acetic acid | HCID 679227 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 75238410 | HCID 75238410 | 18.1% |
Reaction Steps
To a screw-capped test tube, N-(2-thienylcarbonyl)glycine (100 mg, 0.54 mmol), 5-hydroxymethylfuran-2-aldehyde (61 μL, 0.6 mmol), sodium acetate (45 mg, 0.54 mmol) and acetic anhydride (0.32 mL) were added. The test tube was sealed, and it was then stirred at an external temperature of 90° C. Three hours later, the temperature of the reaction solution was returned to room temperature, and water (1.5 mL) was then added thereto. The reaction mixture was extracted with ethyl acetate (5 mL) twice, and organic layers were then gathered. The thus obtained organic layer was washed with water (5 mL) twice, and then with a saturated saline (5 mL) once. Thereafter, the resultant was dried over anhydrous sodium sulfate and was then filtrated, followed by vacuum concentration. The obtained residue was purified by medium-pressure silica gel chromatography (hexane:ethyl acetate=9:1→4:6) and was then dried under reduced pressure, so as to obtain 31 mg of the above-captioned compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09018238B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-43e4ecbbe73f41efa12e6ba30e92866b |
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| Source note | uspto-grants-2015_04 |
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