Hydrochloric Acid → HCID 15237330, compound

HRID 275404Notes

Reaction equation

HRID 275404 reaction equation
O.[OH-].[Li+].[CH3:4][C:5]([C:8]1[CH:9]=[C:10]([S:19][C@@H:20]2[CH2:24][CH2:23][CH2:22][C@H:21]2[S:25][CH2:26][C:27]([O:29]C)=[O:28])[CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])([CH3:7])[CH3:6].O.Cl>CO.[Cl-].[Na+].O>[CH3:7][C:5]([C:8]1[CH:9]=[C:10]([S:19][C@@H:20]2[CH2:24][CH2:23][CH2:22][C@H:21]2[S:25][CH2:26][C:27]([OH:29])=[O:28])[CH:11]=[C:12]([C:15]([CH3:16])([CH3:17])[CH3:18])[C:13]=1[OH:14])([CH3:4])[CH3:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 168937Lithium hydroxide, monohydrateHCID 15287671HCID 15287671, compound

Product 1

HCID 15237330HCID 15237330, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Lithium hydroxide hydrate (1.0 g, 0.025 mole) was added to a solution of the compound of Example 8 (4.13 g, 0.010 mole) in methanol (40 ml). Water (20 ml) was added over 10 minutes to the reaction mixture. 1.0N hydrochloric acid (25 ml) was added slowly to the reaction mixture followed by water (50 ml) and brine (50 ml). The mixture was extracted twice with 75 ml of diethyl ether. The combined diethyl ether extracts were washed with brine (25 ml), dried over anhydrous magnesium sulfate, filtered and concentrated to an oil by a gentle flow of nitrogen gas. The product was purified by silica gel chromatography. The structure was supported by NMR, infrared spectroscopy and elemental analysis.

Workup

  1. extractionThe mixture was extracted twice with 75 ml of diethyl ether
  2. washThe combined diethyl ether extracts were washed with brine (25 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an oil by a gentle flow of nitrogen gas
  6. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e18c974bbc394e7985f8f61487418233
Source dataset
uspto-grants-1995_02
Patent number
US05393764

Reaction notes

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