Hydrochloric Acid → HCID 86744192, compound

HRID 1710221Notes

Reaction equation

HRID 1710221 reaction equation
[CH2:1]([C@@:8]([C@@:31]([CH2:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1)([C@:33]([CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)([C@@:35]([CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)([CH:37](C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[OH:38])[OH:36])[OH:34])[OH:32])([OH:30])[CH:9](C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1>[CH2:58]([C@@:35]([C@@:33]([CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)([C@:31]([CH2:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1)([C@@:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH2:9][OH:10])[OH:30])[OH:32])[OH:34])([OH:36])[CH2:37][OH:38])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86744193HCID 86744193, compound

Product 1

HCID 86744192HCID 86744192, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 78 was dissolved in 20 ml of dioxane, followed by an addition of 2 ml of 1N HCl. The resultant mixture was stirred at 90° C. for 3 hours. After neutralizing the reaction mixture with an aqueous solution of sodium bicarbonate, it was extracted with ether. The extract was washed with water, dried and subjected to flash column chromatography (solvent: 1:2 mixture of ethyl acetate and hexane) to obtain 504 mg of Compound 79 (yield: 50% based on Compound 66).

Workup

  1. extractionwas extracted with ether
  2. washThe extract was washed with water
  3. customdried
  4. additionsubjected to flash column chromatography (solvent: 1:2 mixture of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-1ff1917c02494fddbe53c7519f5bcef1
Source dataset
uspto-grants-1990_08
Patent number
US04952717

Reaction notes

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