Acetic Anhydride → HCID 75238410, compound

HRID 1474481Notes

Reaction equation

HRID 1474481 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=O.O[CH2:14][C:15]1[O:19][C:18]([CH:20]=[O:21])=[CH:17][CH:16]=1.[C:22]([O-])(=[O:24])[CH3:23].[Na+].C(OC(=O)C)(=O)C>O>[C:22]([O:21][CH2:20][C:18]1[O:19][C:15]([CH:14]=[C:9]2[C:10](=[O:11])[O:12][C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[N:8]2)=[CH:16][CH:17]=1)(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 2373325-(Hydroxymethyl)furfuralHCID 517045Sodium AcetateHCID 679227((2-Thienylcarbonyl)amino)acetic acid

Product 1

HCID 75238410HCID 75238410, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  1. customThe test tube was sealed
  2. customThree hours
  3. customwas returned to room temperature
  4. extractionThe reaction mixture was extracted with ethyl acetate (5 mL) twice
  5. washThe thus obtained organic layer was washed with water (5 mL) twice
  6. dry with materialThereafter, the resultant was dried over anhydrous sodium sulfate
  7. filtrationwas then filtrated
  8. concentrationfollowed by vacuum concentration
  9. customThe obtained residue was purified by medium-pressure silica gel chromatography (hexane:ethyl acetate=9:1→4:6)
  10. customwas then dried under reduced pressure

Sources & evidence

ORD record
ord-43e4ecbbe73f41efa12e6ba30e92866b
Source dataset
uspto-grants-2015_04
Patent number
US09018238B2

Reaction notes

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