Sodium Chloride → HCID 56605540, compound

HRID 851364Notes

Reaction equation

HRID 851364 reaction equation
Cl[C@H:2]1[N:5]([C:6](=[C:11]([CH3:13])[CH3:12])[C:7]([O:9][CH3:10])=[O:8])[C:4](=[O:14])[C@@H:3]1[C@@H:15]([O:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)=[O:19])[CH3:16].[CH2:31]([Si](C)(C)C)[CH:32]=[CH2:33].[Cl-].[Na+].C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)(=O)C.F[B-](F)(F)F.[Ag+]>[CH3:12][C:11]([CH3:13])=[C:6]([N:5]1[C@H:2]([CH2:33][CH:32]=[CH2:31])[C@@H:3]([C@@H:15]([O:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[O:19])[CH3:16])[C:4]1=[O:14])[C:7]([O:9][CH3:10])=[O:8]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 69808AllyltrimethylsilaneHCID 516892Sodium BicarbonateHCID 70490013HCID 70490013, compound

Product 1

HCID 56605540HCID 56605540, compound

Reagents, catalysts & solvents 3

HCID 159722Silver tetrafluoroborateCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2-[(3S,4R)-4-chloro-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (180 mg) and allyltrimethylsilane (0.12 ml) in dichloromethane (2 ml) was added silver tetrafluoroborate (240 mg) at -78° C. under a nitrogen atmosphere. The stirring mixture was allowed to warm to 0° C. during 45 minutes and kept at the same temperature for one hour. The mixture was diluted with ethyl acetate (10 ml) and a saturated aqueous sodium chloride was added. The mixture was neutralized with a saturated aqueous sodium bicarbonate, diluted with additional ethyl acetate (20 ml) and filtered through a pad of cellurose powder. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (11 g) eluting with 3-30% ethyl acetate in dichloromethane to give methyl 3-methyl-2-[(3S,4R)-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxo-4-allylazetidin-1-yl]but-2-enoate (47 mg).

Workup

  1. filtrationfiltered through a pad of cellurose powder
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (11 g)
  7. washeluting with 3-30% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-1dd96690477f48be8bd40772ab3f5408
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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