Hydrochloric Acid → HCID 66666314, compound

HRID 1618028Notes

Reaction equation

HRID 1618028 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([C:20]2[CH:25]=[CH:24][C:23]([CH:26]3[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]3)=[CH:22][CH:21]=2)[CH2:10][C:11]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=2)=[O:12])=[C:5]([CH3:39])[CH:4]=1>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([C:20]2[CH:21]=[CH:22][C:23]([CH:26]3[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]3)=[CH:24][CH:25]=2)[CH2:10][C:11]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=2)=[O:12])=[C:5]([CH3:39])[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66666507HCID 66666507, compound

Product 1

HCID 66666314HCID 66666314, compoundYield 108%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrogen chloride solution (4 M in 1,4-dioxane, 0.66 mL, 2.6 mmol) was added to a solution of (R)-tert-butyl 4-(4-(1-(4-chloro-2-methylphenyl)-3-(2-methylpyridin-4-yl)-3-oxopropyl)phenyl)piperidine-1-carboxylate (example 387, step 1; 140 mg, 263 μmol) in ethanol (4 mL) to give a colourless solution, then after 20 h the reaction mixture was partitioned between sat. aq. sodium hydrogencarbonate solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated to afford the title compound (123 mg), which was used without further purification. Off-white foam, MS (ESI+): m/z=433.1 ([M+H]+).

Workup

  1. customto give a colourless solution
  2. customafter 20 h the reaction mixture was partitioned between sat. aq. sodium hydrogencarbonate solution and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-30b2233b1636415cbe8d5aede9e10d8e
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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