Hydrochloric Acid → HCID 20088046, compound

HRID 275406Notes

Reaction equation

HRID 275406 reaction equation
[ClH:1].O[C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[S:9][CH2:10][C:11]([OH:13])=[O:12].O>[Cl-].[Na+].O>[Cl:1][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[S:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

5

Procedure

Concentrated hydrochloric acid (200 ml) was added to the compound of Example 10 (27.1 g, 0.13 mole) and the reaction mixture was stirred at room temperature for 20 hours. Water (100 ml) and brine (50 ml) were added to the reaction mixture. The reaction mixture was extracted three times with 175 ml of diethyl ether. The combined diethyl ether extracts were washed three times with 30 ml of water and dried over anhydrous magnesium sulfate, filtered and concentrated to an oil with a rotary evaporator. The product was purified by silica gel chromatography. The structure was supported by NMR.

Workup

  1. extractionThe reaction mixture was extracted three times with 175 ml of diethyl ether
  2. washThe combined diethyl ether extracts were washed three times with 30 ml of water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an oil with a rotary evaporator
  6. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d2da246670e84de384491e9165012583
Source dataset
uspto-grants-1995_02
Patent number
US05393764

Reaction notes

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