Hydrochloric Acid → HCID 136167084, compound

HRID 1618000Notes

Reaction equation

HRID 1618000 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([C:21]2[CH:26]=[CH:25][C:24]([CH:27]3[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]3)=[CH:23][CH:22]=2)[CH2:10]/[C:11](=[N:19]\[OH:20])/[C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=[C:5]([CH3:40])[CH:4]=1>O1CCOCC1>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([C:21]2[CH:22]=[CH:23][C:24]([CH:27]3[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]3)=[CH:25][CH:26]=2)[CH2:10]/[C:11](/[C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=[N:19]\[OH:20])=[C:5]([CH3:40])[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136166940HCID 136166940, compound

Product 1

HCID 136167084HCID 136167084, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

Hydrogen chloride solution (4 M in 1,4-dioxane, 0.4 mL, 1.6 mmol) was added at room temperature to a solution of (R,E)-tert-butyl 4-(4-(1-(4-chloro-2-methylphenyl)-3-(hydroxy-imino)-3-(2-methylpyridin-4-yl)propyl)phenyl)piperidine-1-carboxylate (example 387; 90 mg, 164 μmol) in 1,4-dioxane (5 mL). The reaction mixture was heated at 50° C. for 17 h, then partitioned between sat. aq. sodium hydrogencarbonate solution and ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and evaporated to produce the title compound (33 mg, 45%). White solid, MS (ESI+): m/z=448.0 ([M+H]+).

Workup

  1. custompartitioned between sat. aq. sodium hydrogencarbonate solution and ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-893fa271d6ee4569b6d64a1764a033f6
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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