Pyridine → HCID 24770478, compound

HRID 746812Notes

Reaction equation

[C:1]([NH:4][C@@H:5]1[C@@H:11]([OH:12])[C@H:10]([OH:13])[C@@H:9]([CH2:14][OH:15])[O:8][CH:6]1[OH:7])(=[O:3])[CH3:2].N1C=CC=CC=1.[C:22](Cl)(=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>CN(C)C=O>[C:1]([NH:4][C@@H:5]1[C@@H:11]([OH:12])[C@H:10]([OH:13])[C@@H:9]([CH2:14][O:15][C:22](=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[O:8][C@@H:6]1[OH:7])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To 0.5 g of N-acetylglucosamine, 5 mL of pyridine and 5 mL of N,N-dimethylformamide were added, and the mixture was heated to 70° C. under stirring, and 0.46 mL of n-octanoyl chloride was dropwise added, and the reaction was carried out for 4 hours. On completion of the reaction, the reaction was extracted with ethyl acetate and washed with 2 mol/L hydrochloric acid, and the obtained ethyl acetate layer was dried over anhydrous magnesium sulfate and then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent; chloroform:methanol=15:1) to obtain 170 mg of 2-acetamido-2-deoxy-6-O-octanoyl-α-D-glucopyranose as a white crystal.

Workup

customOn completion of the reaction
extractionthe reaction was extracted with ethyl acetate
washwashed with 2 mol/L hydrochloric acid
dry with materialthe obtained ethyl acetate layer was dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (elution solvent; chloroform:methanol=15:1)

Sources & evidence

ORD record: ord-26c88553081544babbaab874541c44b7
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07393937B2

Reaction notes

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