HCID 16749199, compound → HCID 16749422, compound

HRID 1279891Notes

Reaction equation

HRID 1279891 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([CH2:24][C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[N:20]=2)[CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>Cl.O1CCOCC1>[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([CH2:24][C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[N:20]=2)[CH2:11][C:12]([OH:14])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 16749199HCID 16749199, compound

Product 1

HCID 16749422HCID 16749422, compoundYield 118.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (3R)-6-cyclohexyl-3-[3-(3-pyridinylmethyl)-1,2,4-oxadiazol-5-yl]hexanoate (Preparation 108) (408 mg, 0.99 mmol) in hydrogen chloride in 1,4-dioxan (4M) (5 ml) was stirred at room temperature for 18 hours. T.l.c. analysis showed reaction had gone >90%. A couple of drops of concentrated hydrochloric acid were added and the reaction mixture was stirred at room temperature for a further 24 hours. The solvent was removed under reduced pressure. A fresh portion of hydrogen chloride in 1,4-dioxan (4M) (4 ml) was added and stirred at room temperature for 4 hours. The solvent was removed under reduced pressure and azeotroped with ethyl acetate and diethylether. The oil was dried under reduced pressure to afford the title compound as a yellow oil (418 mg).

Workup

  1. customreaction
  2. customThe solvent was removed under reduced pressure
  3. additionA fresh portion of hydrogen chloride in 1,4-dioxan (4M) (4 ml) was added
  4. stirringstirred at room temperature for 4 hours
  5. customThe solvent was removed under reduced pressure
  6. customazeotroped with ethyl acetate and diethylether
  7. customThe oil was dried under reduced pressure

Sources & evidence

ORD record
ord-a597cc0474534d4b93b6eb908d7a7b9e
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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