Hydrochloric Acid → HCID 86602926, compound

HRID 901778Notes

Reaction equation

HRID 901778 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:16]([OH:17])[C@@H:15]([CH2:18][OH:19])[O:14][CH:11]([O:12][CH3:13])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.Cl>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH2:1]([O:8][C@H:9]1[C@H:16]([OH:17])[C@@H:15]([CH2:18][O:19][S:26]([C:23]2[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=2)(=[O:28])=[O:27])[O:14][CH:11]([O:12][CH3:13])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 46217146HCID 46217146, compound

Product 1

HCID 86602926HCID 86602926, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

The compound (12.2 g, 45.3 mmol) synthesized in Example 6 (6b) was dissolved in pyridine (100 mL) and p-toluenesulfonyl chloride (13 g, 68.0 mmol) and 4-dimethylaminopyridine (553 mg, 4.53 mmol) were added thereto, followed by stirring of the mixture at room temperature for 12 hours. The reaction mixture was poured to 10% aqueous hydrochloric acid solution (80 mL) under ice cooling, and ethyl acetate (200 mL) and the organic layer was washed with 10% aqueous hydrochloric acid solution (80 mL), saturated aqueous sodium hydrogencarbonate solution (80 mL) and saturated brine (50 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, 5:1-3:1, V/V) to obtain the desired title compound (16.9 g, yield: 88%) as pale yellow amorphous matter.

Workup

  1. washethyl acetate (200 mL) and the organic layer was washed with 10% aqueous hydrochloric acid solution (80 mL), saturated aqueous sodium hydrogencarbonate solution (80 mL) and saturated brine (50 mL)
  2. dry with materialdried with anhydrous sodium sulfate
  3. distillationby distilling off of the solvent under reduced pressure
  4. customThe residue was purified

Sources & evidence

ORD record
ord-889f928d4b2840b3853df065dda3159c
Source dataset
uspto-grants-2008_04
Patent number
US07361744B2

Reaction notes

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