Hydrochloric Acid → HCID 20088046, compound

HRID 1741684Notes

Reaction equation

HRID 1741684 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-82ee9ad8db4b4ba4b0d5bc4f4b5a64a6
Source dataset
uspto-grants-1994_08
Patent number
US05334616

Reaction notes

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