Hydrochloric Acid → HCID 54279934, compound

HRID 2260420Notes

Reaction equation

HRID 2260420 reaction equation
O.[CH3:2][C:3]([C:6]1[CH:7]=[C:8]([S:16][C@@H:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]2[S:23][CH2:24][C:25]([O:27]C)=[O:26])[CH:9]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=1)([CH3:5])[CH3:4].O.[OH-].[Li+].Cl>CO>[CH3:15][C:12]([C:10]1[CH:9]=[C:8]([S:16][C@@H:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]2[S:23][CH2:24][C:25]([OH:27])=[O:26])[CH:7]=[C:6]([C:3]([CH3:2])([CH3:4])[CH3:5])[CH:11]=1)([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 168937Lithium hydroxide, monohydrateHCID 53895626HCID 53895626, compound

Product 1

HCID 54279934HCID 54279934, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Water was added to a solution of the compound of Example 4 (9.2 g, 0.0255 moles) in methyl alcohol (100 ml) until the solution became cloudy. Lithium hydroxide hydrate (1.75 g, 0.0675 moles) was added, and the reaction mixture was stirred at room temperature. Periodically, water was added to make the solution cloudy. After 6 hours, the solution was made acidic with 10% hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extract was dried over sodium sulfate, filtered, and concentrated to give the crude product as an oil. The product was purified by silica gel chromatography. The structure assignment was supported by NMR and elemental analysis.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-95e6b2ca0c7341c28ec7bfa9fb08cdf3
Source dataset
uspto-grants-1995_12
Patent number
US05476944

Reaction notes

Loading…