Chloroform → HCID 86595233, compound

HRID 350761Notes

Reaction equation

HRID 350761 reaction equation
[C:1]([NH:20][CH:21]([CH2:26][O:27][C@@H:28]1[O:60][C@H:59]([CH2:61][O:62][C:63](=[O:70])[C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[C@H:49]([O:50][C:51](=[O:58])[C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C@H:39]([O:40][C:41](=[O:48])[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C@H:29]1[O:30][C:31](=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[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+].C(Cl)(Cl)Cl>N1C=CC=CC=1>[C:1]([NH:20][CH:21]([CH2:26][O:27][C@@H:28]1[O:60][C@H:59]([CH2:61][O:62][C:63](=[O:70])[C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[C@H:49]([O:50][C:51](=[O:58])[C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C@H:39]([O:40][C:41](=[O:48])[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C@H:29]1[O:30][C:31](=[O:38])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[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

5

Reactant 3

HCID 6212ChloroformHCID 66321Lithium iodideHCID 86595232HCID 86595232, compound

Product 1

HCID 86595233HCID 86595233, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 26 mL of pyridine was dissolved 1.4 g of methyl 2-(octadecanoylamino)-3-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyloxy)propionate, 1.7 g of lithium iodide was added to the solution, and the resulting mixture was refluxed under nitrogen atmosphere for 4 hours. Chloroform was added to the reaction mixture, the resulting mixture was washed with 2 mol/L of hydrochloric acid, the chloroform layer was dried over anhydrous magnesium sulfate, and then, the solvent was removed under reduced pressure. The finally obtained residue was purified by silica gel chromatography (Eluent; chloroform: methanol=60:1) to obtain 940 mg of 2-(octadecanoylamino)-3-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyloxy) propionic acid.

Workup

  1. additionwas added to the solution
  2. temperaturethe resulting mixture was refluxed under nitrogen atmosphere for 4 hours
  3. washthe resulting mixture was washed with 2 mol/L of hydrochloric acid
  4. dry with materialthe chloroform layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe finally obtained residue was purified by silica gel chromatography (Eluent; chloroform: methanol=60:1)

Sources & evidence

ORD record
ord-06a05e2bc0ed459297465266b30d1bf9
Source dataset
uspto-grants-2007_02
Patent number
US07183261B2

Reaction notes

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