Hydrochloric Acid → HCID 178520679, compound

HRID 724216Notes

Reaction equation

HRID 724216 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][C:11]([C:13]1[N:14]=[CH:15][N:16](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:17]=1)=[O:12].Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[OH:7][CH2:8][CH2:9][CH2:10][C:11]([C:13]1[N:14]=[CH:15][NH:16][CH:17]=1)=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21879617HCID 21879617, compound

Product 1

HCID 178520679HCID 178520679, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(Tetrahydro-2H-pyran-2-yloxy)-1-(1-trityl-1H-imidazol-4-yl)butan-1-one (28.51 g) and 6 N hydrochloric acid (17.5 ml) were dissolved in tetrahydrofuran (200 ml) and the mixture was stirred at room temperature for 3 h. Sodium bicarbonate (8.82 g) was added to the reaction mixture, and after removal of the precipitate by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; ethyl acetate:methanol=4:1) and recrystallized from methanol/ethyl acetate/diethyl ether to give the title compound (9.38 g) as a pale yellow powder.

Workup

  1. customafter removal of the precipitate
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent; ethyl acetate:methanol=4:1)
  5. customrecrystallized from methanol/ethyl acetate/diethyl ether

Sources & evidence

ORD record
ord-e6742cf38b1f4156bb9d5bf863894544
Source dataset
uspto-grants-2006_11
Patent number
US07141598B2

Reaction notes

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