Lithium iodide → HCID 68866919, compound

HRID 350759Notes

Reaction equation

HRID 350759 reaction equation
[C:1]([NH:20][CH:21]([CH2:26][S:27][C@@H:28]1[O:45][C@H:44]([CH2:46][O:47][C:48](=[O:50])[CH3:49])[C@H:39]([O:40][C:41](=[O:43])[CH3:42])[C@H:34]([O:35][C:36](=[O:38])[CH3:37])[C@H:29]1[O:30][C:31](=[O:33])[CH3:32])[C:22]([O:24]C)=[O:23])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[I-].[Li+]>N1C=CC=CC=1>[C:1]([NH:20][CH:21]([CH2:26][S:27][C@@H:28]1[O:45][C@H:44]([CH2:46][O:47][C:48](=[O:50])[CH3:49])[C@H:39]([O:40][C:41](=[O:43])[CH3:42])[C@H:34]([O:35][C:36](=[O:38])[CH3:37])[C@H:29]1[O:30][C:31](=[O:33])[CH3:32])[C:22]([OH:24])=[O:23])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 68866885HCID 68866885, compound

Product 1

HCID 68866919HCID 68866919, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 6 mL of pyridine was dissolved 313 mg of methyl 2-(octadecanoylamino)-3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosylthio)propionate, 515 mg of lithium iodide was added to the solution and the resulting mixture was refluxed under nitrogen atmosphere for 4 hours. The reaction mixture was extracted with ethyl acetate, washed with 2 mol/L of hydrochloric acid, the ethyl acetate layer was dried over anhydrous magnesium sulfate, and then, the solvent was removed under reduced pressure. The finally obtained residue was purified by medium pressure column chromatography (Eluent; chloroform:methanol=15:1) to obtain 247 mg of 2-(octadecanoylamino)-3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosylthio) propionic acid.

Workup

  1. additionwas added to the solution
  2. temperaturethe resulting mixture was refluxed under nitrogen atmosphere for 4 hours
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washwashed with 2 mol/L of hydrochloric acid
  5. dry with materialthe ethyl acetate layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe finally obtained residue was purified by medium pressure column chromatography (Eluent; chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-a5b6cfbfb29d4f0483c86c481a6f5995
Source dataset
uspto-grants-2007_02
Patent number
US07183261B2

Reaction notes

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