Hydrochloric Acid → HCID 86602944, compound

HRID 901805Notes

Reaction equation

HRID 901805 reaction equation
[C@@H:1]1([O:12][C@@H:13]2[C@@H:22]([CH2:23][OH:24])[O:21][CH:16]([O:17][CH2:18][CH:19]=[CH2:20])[C@H:15]([OH:25])[C@H:14]2[OH:26])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl.CCl>N1C=CC=CC=1>[C:27]([C@@:15]1([OH:25])[C@@:14]([C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([OH:26])[C@H:13]([O:12][C@@H:1]2[O:9][C@H:8]([CH2:10][O:11][C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@@H:6]([O:7][C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:4]([O:5][C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:2]2[O:3][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@@H:22]([CH2:23][O:24][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:21][CH:16]1[O:17][CH2:18][CH:19]=[CH2:20])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6327Methyl ChlorideHCID 7412Benzoyl chlorideHCID 67157178HCID 67157178, compound

Product 1

HCID 86602944HCID 86602944, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The compound (4.0 g, 10.46 mmol) synthesized in Example 2 (2a) was dissolved in pyridine (30 mL) and benzoyl chloride (12.1 mL, 104.24 mmol) was added thereto under ice-cooling, followed by stirring of the mixture at room temperature for 14 hours. The reaction mixture was poured to 10% aqueous hydrochloric acid solution (20 mL) and methyl chloride (20 mL) and the organic layer was washed with 10% aqueous hydrochloric acid solution (20 mL), saturated aqueous sodium hydrogencarbonate solution (20 mL) and saturated brine (20 mL) and dried with anhydrous sodium sulfate, followed by distilling off of the solvent under reduced pressure. The residue was purified using silica gel flash column chromatography (hexane:ethyl acetate, 5:1-5:2, V/V) to obtain the desired title compound (8.10 g, yield 70%) as a colorless oil.

Workup

  1. temperatureunder ice-cooling
  2. washthe organic layer was washed with 10% aqueous hydrochloric acid solution (20 mL), saturated aqueous sodium hydrogencarbonate solution (20 mL) and saturated brine (20 mL)
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationby distilling off of the solvent under reduced pressure
  5. customThe residue was purified

Sources & evidence

ORD record
ord-aa809817d1264238b2fbebe219cdfd5e
Source dataset
uspto-grants-2008_04
Patent number
US07361744B2

Reaction notes

Loading…