Sodium → (3R)-6-cyclohexyl-3-[3-(1,1-dioxido-2-isothiazolidinyl)-1,2,4-oxadiazol-5-yl]hexanoic acid

HRID 1350215Notes

Reaction equation

HRID 1350215 reaction equation
[Na].Cl[CH2:3][CH2:4][CH2:5][S:6]([NH:9][C:10]1[N:14]=[C:13]([C@H:15]([CH2:24][CH2:25][CH2:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])[O:12][N:11]=1)(=[O:8])=[O:7]>CO>[CH:27]1([CH2:26][CH2:25][CH2:24][C@@H:15]([C:13]2[O:12][N:11]=[C:10]([N:9]3[CH2:3][CH2:4][CH2:5][S:6]3(=[O:8])=[O:7])[N:14]=2)[CH2:16][C:17]([OH:19])=[O:18])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 5360545Sodium2×HCID 69432927tert-butyl(3R)-3-(3-{[(3-chloropropyl)sulfonyl]amino}-1,2,4-oxadiazol-5-yl)-6-cyclohexylhexanoate

Product 1

HCID 69427413(3R)-6-cyclohexyl-3-[3-(1,1-dioxido-2-isothiazolidinyl)-1,2,4-oxadiazol-5-yl]hexanoic acidYield 105.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium metal (114 mg, 5.00 mmol) was added in portions to MeOH (10 ml) at 0° C. and stirred until all of the sodium had dissolved (˜10 minutes). A solution of tert-butyl(3R)-3-(3-{[(3-chloropropyl)sulfonyl]amino}-1,2,4-oxadiazol-5-yl)-6-cyclohexylhexanoate (preparation 45) (245 mg, 0.50 mmol) in MeOH (3 ml) was added to the reaction mixture and was stirred under a nitrogen atmosphere for 3 days warming to room temperature over this time. The reaction was quenched with H2O and the solvent removed under reduced pressure. The residue was diluted with water and acidified with 2M HCl (pH-3) and extracted with Et2O followed by EtOAc. The organic extracts were combined, dried over anhydrous MgSO4 and filtered. The solvent was removed under reduced pressure to afford the title compound as a colourless oil (203 mg, 98%).

Workup

  1. dissolutionhad dissolved (˜10 minutes)
  2. customThe reaction was quenched with H2O
  3. customthe solvent removed under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted with Et2O
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cd38576545d942eaa16d22fd8c8792b5
Source dataset
uspto-grants-2007_05
Patent number
US07214694B2

Reaction notes

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