Sodium Bicarbonate → HCID 57639120, compound

HRID 2111528Notes

Reaction equation

HRID 2111528 reaction equation
[CH:1]([Mg]Br)([CH3:3])[CH3:2].[CH:6]([N:19]1[CH2:22][C:21](=[O:23])[CH2:20]1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([O-])(O)=O.[Na+]>C1COCC1>[CH:6]([N:19]1[CH2:22][C:21]([CH:1]([CH3:3])[CH3:2])([OH:23])[CH2:20]1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 37355581-(Diphenylmethyl)azetidin-3-oneHCID 178418365HCID 178418365, compound

Product 1

HCID 57639120HCID 57639120, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 1.0 M isopropylmagnesium bromide in THF (5.0 mL, 5.0 mmol), 1-benzhydryl-azetidin-3-one (237 mg, 1 mmol) in THF (5 mL) was added dropwise at 0° C. The reaction mixture was stirred at 0° C. for 1 hr. Then it was added 10% NaHCO3 solution and extracted with ether (2×30 mL). The organic layers were combined, dried (MgSO4) and concentrated to give an orange oil. The crude product was purified by Prep. HPLC column using CH3CN—H2O-ammonium acetate solvent system. Fractions were collected and concentrated. Then it was extracted with ethyl acetate (2×30 mL). The organic layers were combined, dried (MgSO4) and concentrated to give a light yellow oil as Grignard reaction product. (80 mg, 28% yield). MS m/z 282(MH+), Retention time: 1.485 min. 1H NMR (300 MHz, MeOD) δ ppm 0.93 (d, J=6.95 Hz, 6 H) 1.90-2.04 (m, 1 H) 3.00 (d, J=9.15 Hz, 2 H) 3.28 (d, J=9.15 Hz, 2 H) 4.49 (s, 1 H) 7.14-7.22 (m, 2 H) 7.23-7.33 (m, 4 H) 7.37-7.46 (m, 4 H).

Workup

  1. extractionextracted with ether (2×30 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto give an orange oil
  5. customThe crude product was purified by Prep
  6. customFractions were collected
  7. concentrationconcentrated
  8. extractionThen it was extracted with ethyl acetate (2×30 mL)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customto give a light yellow oil
  12. customas Grignard reaction product

Sources & evidence

ORD record
ord-0ea70c56c8cb425ebb2ff98de0d74918
Source dataset
uspto-grants-2009_04
Patent number
US07521442B2

Reaction notes

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