Pyridine → HCID 69270369, compound

HRID 746813Notes

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:38])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>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:38])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[O:8][C@@H:6]1[OH:7])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To 1 g of N-acetylglucosamine, 5 mL of pyridine and 15 mL of N,N-dimethylformamide were added, and the mixture was heated to 70° C. under stirring and 1.37 mL of palmitoyl chloride was dropwise added, and the reaction was carried out for 4 hours. On completion of the reaction, after extracting with ethyl acetate and washing with 2 mol/L hydrochloric acid, the 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 710 mg of 2-acetamido-2-deoxy-6-O-palmitoyl-α-D-glucopyranose as a white crystal.

Workup

customOn completion of the reaction
extractionafter extracting with ethyl acetate
washwashing with 2 mol/L hydrochloric acid
dry with materialthe 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-ca9b18613cc2481cbec58b30dec84c68
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07393937B2

Reaction notes

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