Hydrochloric Acid → HCID 23147014, compound

HRID 495284Notes

Reaction equation

HRID 495284 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[C:4]([CH2:17][CH2:18][O:19][CH3:20])[C:3]=1[C:21](=O)[CH3:22].C(N(CC)CC)C.C(Cl)(=O)OC.[BH4-].[Na+].Cl>O1CCCC1.CO.O>[CH2:21]([C:3]1[C:2]([OH:1])=[CH:7][C:6]([OH:8])=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)[C:4]=1[CH2:17][CH2:18][O:19][CH3:20])[CH3:22]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 23147513HCID 23147513, compound

Product 1

HCID 23147014HCID 23147014, compoundYield 18%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 116 obtained in Example 116 was dissolved in tetrahydrofuran (10 mL), and triethylamine (0.35 mL, 2.5 mmol) and methyl chlorocarbonate (0.18 mL, 2.3 mmol) were added thereto and stirred at room temperature for 1 hour. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in tetrahydrofuran (10 mL), and under stirring with ice-cooling, aqueous solution (5 mL) of sodium borohydride (150 mg, 4.0 mmol) was dropwise added thereto, and stirred for 1 hour. Water was added to the reaction solution, and extracted twice with ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through silica gel column chromatography (ethyl acetate/n-hexane 1/1) to obtain a crude product. Methanol solution (10 mL) of 7 mol/L hydrochloric acid was added to the resulting crude product, and stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (ethyl acetate/n-hexane=1/4 to 1/1) to obtain Compound 118 (53 mg, 18%)

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe resulting residue was dissolved in tetrahydrofuran (10 mL)
  4. stirringunder stirring with ice-
  5. temperaturecooling
  6. stirringstirred for 1 hour
  7. extractionextracted twice with ethyl acetate
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated away under reduced pressure
  10. customThe resulting residue was purified through silica gel column chromatography (ethyl acetate/n-hexane 1/1)
  11. customto obtain a crude product
  12. stirringstirred at room temperature for 2 hours
  13. concentrationThe reaction solution was concentrated under reduced pressure
  14. customthe resulting residue was purified through silica gel column chromatography (ethyl acetate/n-hexane=1/4 to 1/1)

Sources & evidence

ORD record
ord-6b3e0ca788ab426690088be29eca1301
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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