Hydrochloric Acid → HCID 60077591, compound

HRID 1350212Notes

Reaction equation

HRID 1350212 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:16]2[O:20][N:19]=[C:18]([CH:21]3[CH2:24][N:23]([S:25]([CH3:28])(=[O:27])=[O:26])[CH2:22]3)[N:17]=2)[CH2:11][C:12]([O:14]C)=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O[Li].O.Cl>O1CCOCC1.O>[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:16]2[O:20][N:19]=[C:18]([CH:21]3[CH2:22][N:23]([S:25]([CH3:28])(=[O:26])=[O:27])[CH2:24]3)[N:17]=2)[CH2:11][C:12]([OH:14])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 60077654HCID 60077654, compound

Product 1

HCID 60077591HCID 60077591, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl(3R)-6-cyclohexyl-3-{3-[1-(methylsulfonyl)-3-azetidinyl]-1,2,4-oxadiazol-5-yl}hexanoate (preparation 38) (780 mg, 1.05 mmol) in dioxan (20 ml) and H2O (10 ml) was treated with LiOH.H2O (218 mg, 5.2 mmol) and stirred at room temperature for 2.25 hours. The reaction mixture was acidified with 2M HCl (20 ml) and extracted with EtOAc. The organic extract was washed with H2O and the solvent was removed under reduced pressure. The oil was purified on a silica column eluting with a solvent gradient of DCM:MeOH:AcOH (100:0:0) gradually changing to (90:10:1) to afford a colourless oil which solidified on standing. The solid was triturated with pentane, filtered off and dried under reduced pressure to afford the title compound as a white solid (372 mg, 78%).

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with H2O
  4. customthe solvent was removed under reduced pressure
  5. customThe oil was purified on a silica column
  6. washeluting with a solvent gradient of DCM:MeOH:AcOH (100:0:0)
  7. customto afford a colourless oil which
  8. customThe solid was triturated with pentane
  9. filtrationfiltered off
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-ee9a0704108d4921b565598c89711f69
Source dataset
uspto-grants-2007_05
Patent number
US07214694B2

Reaction notes

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