HCID 59909811, compound → HCID 59909801, compound

HRID 1279880Notes

Reaction equation

HRID 1279880 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][S:25]([CH2:28][CH2:29][CH3:30])(=[O:27])=[O:26])[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][S:25]([CH2:28][CH2:29][CH3:30])(=[O:27])=[O:26])[N:20]=2)[CH2:11][C:12]([OH:14])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 59909811HCID 59909811, compound

Product 1

HCID 59909801HCID 59909801, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (3R)-6-cyclohexyl-3-{3-[(propylsulfonyl)methyl]-1,2,4-oxadiazol-5-yl}hexanoate (Preparation 96) (371 mg, 0.84 mmol) in hydrogen chloride in 1,4-dioxan (4M) (4 ml) was stirred at room temperature for 24 hours. The solvent was removed under reduced pressure. The solid was dissolved in fresh hydrogen chloride in 1,4-dioxan (4M) and stirred at room temperature for 3 hours. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulphate, filtered and the solvent was removed under reduced pressure to afford the title compound as a yellow oil (313 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe solid was dissolved in fresh hydrogen chloride in 1,4-dioxan (4M)
  3. customThe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with saturated sodium hydrogen carbonate solution and brine
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7dd90267125447f5ae4d84d803c0ccca
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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