1,4-Dioxane hydrochloride → HCID 117839269, compound

HRID 1477636Notes

Reaction equation

HRID 1477636 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]2[C@@H:15]([O:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH:11]=2)=[N:6][C:7]=1[O:8][CH3:9].Cl.O1CCOCC1>CO>[C:17]([O:16][C@@H:15]1[C:10]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[C:7]([O:8][CH3:9])[N:6]=2)=[CH:11][CH2:12][NH:13][CH2:14]1)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 117849075HCID 117849075, compound

Product 1

HCID 117839269HCID 117839269, compoundYield 127.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol solution (1.0 mL) of tert-butyl (R)-5-chloro-6-methoxy-5′-(pivaloyloxy)-5′,6′-dihydro-[2,4′-bipyridine]-1′(2′H)-carboxylate (1.35 g, 3.18 mmol) synthesized in Reference Synthesis Example 142, 4 M hydrogen chloride/1,4-dioxane (15 mL) was added and the resultant mixture was stirred at room temperature for 5 minutes. After completion of the reaction, the reaction solution was concentrated under reduced pressure and saturated sodium bicarbonate aqueous solution and water were added to the concentrated solution, followed by extraction from the resultant mixture with ethyl acetate. The organic layer was concentrated under reduced pressure to obtain a crude product of the title compound (1.32 g).

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. concentrationthe reaction solution was concentrated under reduced pressure and saturated sodium bicarbonate aqueous solution and water
  4. additionwere added to the concentrated solution
  5. extractionfollowed by extraction from the resultant mixture with ethyl acetate
  6. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cde83dbd09d34a8fad044e25fbbdf49e
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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