Sodium Hydroxide → HCID 67786490, compound

HRID 2210707Notes

Reaction equation

HRID 2210707 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[CH:7]=[C:8]([CH2:13][O:14][CH:15]2[CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:17]([CH3:25])[C:16]2=[O:26])[CH:9]=[C:10]([CH3:12])[CH:11]=1.[OH-:27].[Na+].S([O-])([O-])(=O)=[O:30].[Mg+2]>O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].ClCCl.O>[C:16]([OH:26])(=[O:30])[C:15]([OH:14])=[O:27].[CH3:12][C:10]1[CH:9]=[C:8]([CH2:13][O:14][C@H:15]2[CH2:16][N:17]([CH3:25])[C@H:18]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:7]=[C:6]([CH3:5])[CH:11]=1

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 6451240Aluminum(III) ChlorideHCID 19379394HCID 19379394, compound

Product 1

HCID 67786490HCID 67786490, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 21226445Aluminium lithium hydrideSolvent

Procedure

To a solution of aluminium chloride (0.29 g) in tetrahydrofuran (10 ml), lithium aluminium hydride (2.2 ml) was carefully added dropwise. After the reaction mixture had been stirred for 1 h, a solution of 3-((3,5-dimethylphenyl)methyloxy)-1-methyl-4-phenyl azetidin-2-one (0.66 g) in tetrahydrofuran (5 ml) was added via syringe. After a further hour water (1 ml) was carefully added dropwise followed by dropwise addition of 2N sodium hydroxide (1 ml). Dichloromethane (75 ml) was added followed by magnesium sulphate. After stirring for 30 minutes the solution was filtered. The organic phase was dried (MgSO4), filtered and evaporated. The crude material was chromatographed on flash silica and eluted with ethyl acetate:petrol 1:1. The resulting compound was dissolved in ether and an ethereal solution of oxalic acid was added dropwise to give the title compound as a white solid, m.p.=147°-149° C. 1H NMR (360 MHz, DMSO) δ7.57 (2H, m), 7.43 (3H, m), 6.86 (1H, s), 6.62 (1H, s), 5.02 (m), 4.55 (m), 4.17 (1H, d, J=11 Hz), 3.94 (1H, d. J=11 Hz), 3.83 (1H, s), 2.61 (1H, s), 2.19 (1H, s); m/z (CI+) 282 (MH). Found: C, 67.75; H, 7.00; N, 3.78. Calcd for C19H23O1N1 . [COOH]2 : C, 67.91; H, 6.78; N, 3.77%.

Workup

  1. stirringAfter stirring for 30 minutes the solution
  2. filtrationwas filtered
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude material was chromatographed on flash silica
  7. washeluted with ethyl acetate:petrol 1:1
  8. dissolutionThe resulting compound was dissolved in ether
  9. additionan ethereal solution of oxalic acid was added dropwise

Sources & evidence

ORD record
ord-d713553276304e63ac3a96c00101abf6
Source dataset
uspto-grants-1995_10
Patent number
US05459270

Reaction notes

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