Hydrochloric Acid → HCID 86746898, compound

HRID 1587108Notes

Reaction equation

HRID 1587108 reaction equation
[OH:1][CH2:2][C@H:3]1[O:8][C:6](=[O:7])[CH2:5][C@@H:4]1[CH3:9].[S:10](Cl)([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:12])=[O:11].Cl>N1C=CC=CC=1>[S:10]([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)([OH:1])(=[O:12])=[O:11].[CH3:9][C@@H:4]1[C@@H:3]([CH2:2][O:1][S:10]([C:13]2[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[O:8][C:6](=[O:7])[CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 11768599HCID 11768599, compound

Product 1

HCID 86746898HCID 86746898, compoundYield 106.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 60 ml of anhydrous pyridine, 7.9 g of (3S, 4S)-5-hydroxy-3-methylpentan-4-olide (60.8 mmol) obtained in step [B] were dissolved. To the resultant solution, 15.1 g of tosyl chloride (79.0 mmol) were added with cooling by ice. The obtained mixture was stirred at room temperature overnight. The reacted solution was poured into a diluted hydrochloric acid solution which had been cooled, and extracted with methylene chloride. The obtained extract was washed with water and a saturated sodium chloride aqueous solution, in this order, and dried with anhydrous magnesium sulfate. Next, the obtained solution was filtered, and the obtained filtrate was concentrated. The obtained residue was purified via silica gel column chromatography (n-hexane:ethyl acetate=5:1 to 1:2) to obtain 14.8 g of (3S,4S)-3-methyl-5-tosyloxypentan-4-olide (tosylate) (yield: 85.5%). This product exhibited the following physical properties:

Workup

  1. temperaturewith cooling by ice
  2. temperaturehad been cooled
  3. extractionextracted with methylene chloride
  4. extractionThe obtained extract
  5. washwas washed with water
  6. dry with materiala saturated sodium chloride aqueous solution, in this order, and dried with anhydrous magnesium sulfate
  7. filtrationNext, the obtained solution was filtered
  8. concentrationthe obtained filtrate was concentrated
  9. customThe obtained residue was purified via silica gel column chromatography (n-hexane:ethyl acetate=5:1 to 1:2)

Sources & evidence

ORD record
ord-bddd0a9803734476a8d789c2dcc9b7d3
Source dataset
uspto-grants-1993_06
Patent number
US05216177

Reaction notes

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