Acetic Anhydride → HCID 69827825, compound

HRID 2297675Notes

Reaction equation

HRID 2297675 reaction equation
[CH2:1]([C:3]1[O:7][N:6]=[C:5]([C@H:8]2[O:12][CH:11]([OH:13])[C@H:10]([OH:14])[C@@H:9]2[OH:15])[CH:4]=1)[CH3:2].C(O[C:20](=[O:22])[CH3:21])(=O)C>N1C=CC=CC=1>[C:3]([O:15][C@H:9]1[C@@H:10]([O:14][C:11](=[O:12])[CH3:10])[CH:11]([O:13][C:20](=[O:22])[CH3:21])[O:12][C@@H:8]1[C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[O:7][N:6]=1)(=[O:7])[CH3:1]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 45093395(3R,4S,5R)-5-(5-Ethyl-3-isoxazolyl)tetrahydro-2,3,4-furantriol

Product 1

HCID 69827825HCID 69827825, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
22 °C

Procedure

(3R,4S,5R)-5-(5-ethylisoxazol-3-yl)tetrahydrofuran-2,3,4-triol isomer 1 (150 mg) was dissolved in pyridine (4 ml) and the mixture treated with acetic anhydride (0.983 ml). The resulting solution was stirred at 22° C. for 18 h. The mixture was concentrated in vacuo to afford a brown oil. Purification by chromatography on silica gel (Varian Bondelut SiO2 cartridge), eluting with (i) dichloromethane, (ii) ether (iii) ethyl acetate, afforded the title compound as a pale yellow solid (142 mg).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto afford a brown oil
  3. customPurification by chromatography on silica gel (Varian Bondelut SiO2 cartridge)
  4. washeluting with (i) dichloromethane, (ii) ether (iii) ethyl acetate

Sources & evidence

ORD record
ord-1ce3de75e22d4ce6a996a3267fce5f7a
Source dataset
uspto-grants-2002_12
Patent number
US06492348B1

Reaction notes

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