Hydrochloric Acid → HCID 86753791, compound

HRID 1417601Notes

Reaction equation

HRID 1417601 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[CH2:24][C@:23]3([CH3:37])[C@@H:25]([CH3:36])[CH2:26][CH2:27][C@H:28]4[C:29]([CH3:35])([CH3:34])[C@@H:30]([OH:33])[CH2:31][CH2:32][C@@:22]34[O:21][C:11]=2[C:12]2[CH:13]([O:19]C)[NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O>O1CCOCC1>[CH2:1]([O:8][C:9]1[C:10]2[CH2:24][C@:23]3([CH3:37])[C@@H:25]([CH3:36])[CH2:26][CH2:27][C@H:28]4[C:29]([CH3:35])([CH3:34])[C@@H:30]([OH:33])[CH2:31][CH2:32][C@@:22]34[O:21][C:11]=2[C:12]2[CH:13]([OH:19])[NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86753792HCID 86753792, compound

Product 1

HCID 86753791HCID 86753791, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the above Compound (29b) (439 mg, 0.87 mmol) in dioxane (15 ml) was added 0.15 ml of 0.1N HCl, and the mixture stirred at room temperature for 2 hours. Water was added to the reaction, and extracted with ethyl acetate. The extract was washed with 5% sodium carbonate aqueous solution and saturated brine, and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by a silica gel column chromatography (silica gel 15 g; toluene:ethyl acetate=1:2) to give 276 mg (62%) of Compound (29a).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with 5% sodium carbonate aqueous solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe residue was purified by a silica gel column chromatography (silica gel 15 g; toluene:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-0b7bd6e541174ddfbaeaed9c06c74724
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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