Hydrochloric Acid → HCID 68196365, compound

HRID 1626795Notes

Reaction equation

HRID 1626795 reaction equation
[OH:1][C:2]1[C:3]([C:34]([NH:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[O:35])=[N:4][C:5]([CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]4[CH:28]=[CH:27][C:26]([CH2:29][O:30][CH2:31][O:32]C)=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[N:6][C:7]=1[CH3:8].Cl.O1CCOC[CH2:45]1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[C:31]([O:30][CH2:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][C:19]2[CH:20]=[CH:21][C:16]([N:13]3[CH2:12][CH2:11][CH:10]([CH2:9][C:5]4[N:4]=[C:3]([C:34]([NH:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[O:35])[C:2]([OH:1])=[C:7]([CH3:8])[N:6]=4)[CH2:15][CH2:14]3)=[CH:17][CH:18]=2)=[CH:24][CH:25]=1)(=[O:32])[CH3:45]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 68196367HCID 68196367, compound

Product 1

HCID 68196365HCID 68196365, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl {[(5-hydroxy-2-{[1-(4-{4-[(methoxymethoxy)methyl]benzyl}phenyl)piperidin-4-yl]methyl}-6-methylpyrimidin-4-yl)carbonyl]amino}acetate (1.1 g, 1.9 mmol) was dissolved in ethyl acetate (14 mL), and a solution of hydrogen chloride in dioxane (4 M, 7 mL, 28 mmol) was added at room temperature, followed by stirring at the same temperature for 12 hours. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, followed by extraction with ethyl acetate, and subsequently the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.60 (hexane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (0.74 g, 1.3 mmol) as a yellow oil (yield 69%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialsubsequently the organic layer was dried over anhydrous sodium sulfate
  3. distillationAfter the solvent was distilled off under reduced pressure
  4. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  5. concentrationa fraction corresponding to the Rf value=0.60 (hexane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2ef1e46930f14849a443631418b1ca26
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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