tert-butyl (3R)-6-cyclohexyl-3-(3-{[methyl(methylsulfonyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoate → (3R)-6-cyclohexyl-3-(3-{[methyl(methylsulfonyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoic acid

HRID 2084446Notes

Reaction equation

HRID 2084446 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][N:25]([CH3:30])[S:26]([CH3:29])(=[O:28])=[O:27])[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][N:25]([CH3:30])[S:26]([CH3:29])(=[O:28])=[O:27])[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 16748327tert-butyl (3R)-6-cyclohexyl-3-(3-{[methyl(methylsulfonyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoate

Product 1

HCID 16748570(3R)-6-cyclohexyl-3-(3-{[methyl(methylsulfonyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoic acid

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 313Hydrochloric AcidSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of tert-butyl (3R)-6-cyclohexyl-3-(3-{[methyl(methylsulfonyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoate (preparation 6) (264 mg, 0.60 mmol) in 4M HCl in dioxan (2 ml) was stirred at room temperature for 20 hours. Further 4M HCl in dioxan (2 ml) was added and stirred for a further 3 hours. A few drops of concentrated HCl was added and the reaction mixture was stirred at room temperature for 18 hours. The solvent was removed under reduced pressure to afford the title compound (245 mg—contained some dioxan as impurity).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 18 hours
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4094499ecfd34c2598fbe5b6f45c3ace
Source dataset
uspto-grants-2004_04
Patent number
US06716861B2

Reaction notes

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