Hydrochloric Acid → HCID 58043182, compound

HRID 1618056Notes

Reaction equation

HRID 1618056 reaction equation
[OH:1]/[N:2]=[C:3](/[C:32]1[CH:37]=[CH:36][C:35](=[O:38])[N:34]([CH3:39])[CH:33]=1)\[CH2:4][C@H:5]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12].Cl.O1CCOCC1.C(=O)([O-])O.[Na+]>C(O)C>[OH:1]/[N:2]=[C:3](/[C:32]1[CH:37]=[CH:36][C:35](=[O:38])[N:34]([CH3:39])[CH:33]=1)\[CH2:4][C@H:5]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 58043543HCID 58043543, compound

Product 1

HCID 58043182HCID 58043182, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R,E)-tert-Butyl 4-(4-(3-(hydroxyimino)-3-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-1-o-tolylpropyl)phenyl)piperidine-1-carboxylate (example 506, 30 mg) was dissolved in ethanol (0.8 mL) and hydrochloric acid solution (4.0 M in 1,4-dioxane (170 μl, 680 μmol) was added, then after 14 h the reaction mixture was poured onto aq. sat. sodium hydrogencarbonate solution and extracted 2 times with dichloromethane. The combined organic layers were washed with brine dried over magnesium sulfate, filtered and evaporated. The residue was triturated with ethyl acetate/heptane to afford the title compound (12 mg, 41%). Light yellow solid; MS (ESI+): m/z=: 430.5 [M+H]+).

Workup

  1. extractionextracted 2 times with dichloromethane
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was triturated with ethyl acetate/heptane

Sources & evidence

ORD record
ord-5d4a0fa7dc01428396de31dadd7f7366
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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