Hydrochloric Acid → HCID 18734917, compound

HRID 843732Notes

Reaction equation

HRID 843732 reaction equation
C(I)I.[Si:4]([N:11]1[C@H:14]([CH:15]=O)[CH2:13][C:12]1=[O:17])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5].[CH2:18](OCC)C.Cl>O1CCCC1.[Zn].CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Si:4]([N:11]1[C@H:14]([CH:15]=[CH2:18])[CH2:13][C:12]1=[O:17])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6346DiiodomethaneHCID 10899970HCID 10899970, compound

Product 1

HCID 18734917HCID 18734917, compound

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of zinc (11.9 g) in tetrahydrofuran (215 ml) was added titanium (IV) isopropoxide (6.0 ml) at ambient temperature and the resultant mixture was stirred for 1 hour. A solution of methyleneiodide (8.1 ml) was then added to the mixture was stirred for 30 minutes. To the resultant mixture was added dropwise a solution of (S)-N-tert-butyldimethylsilyl-4-formyl-2-azetidinone (4.3 g) in tetrahydrofuran (130 ml) and stirred for 2 hours. The mixture was poured into a mixture of diethyl ether (500 ml) and 1N HCl (300 ml). The organic layer was washed with water, saturated aqueous NaHCO3 solution and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatograph on silica gel eluting with (EtOAc:n-hexane=1:10) to give (S)-N-tert-butyldimethylsilyl-4-vinyl-2-azetidinone (2.13 g) as a colorless oil.

Workup

  1. stirringstirred for 2 hours
  2. washThe organic layer was washed with water, saturated aqueous NaHCO3 solution and brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by chromatograph on silica gel eluting with (EtOAc:n-hexane=1:10)

Sources & evidence

ORD record
ord-c8920224868044bdacfd8555125914de
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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