Sodium Chloride → HCID 54067472, compound

HRID 1719269Notes

Reaction equation

HRID 1719269 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[N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25].C[Si]([CH2:30][C:31](=[CH2:37])[CH2:32][C:33]([O:35][CH3:36])=[O:34])(C)C.[Cl-].[Na+].C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)(=O)C.F[B-](F)(F)F.[Ag+]>[CH3:36][O:35][C:33]([CH2:32][C:31](=[CH2:30])[CH2:37][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[N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25])=[O:34]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 11769254AG-G-75877HCID 12959530HCID 12959530, compound

Product 1

HCID 54067472HCID 54067472, compoundYield 79.6%

Reagents, catalysts & solvents 3

HCID 159722Silver tetrafluoroborateCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Silver tetrafluoroborate (323 mg) was added to a stirred mixture of methyl 2-[(3S,4R)-4-chloro-2-oxo-3-phthalimidoazetidin-1-yl]-3-methylbut-2-enoate (500 mg) and methyl 3-(trimethylsilylmethyl)-but-3-enoate (460 mg) in dichloromethane (2.5 ml) at -78° C. under a nitrogen atmosphere. The stirring mixture was gradually allowed to warm to 0° C. during one hour and kept at 0° C. for 1.5 hours. A saturated aqueous sodium chloride (2 ml) was added and the heterogeneous mixture was brought to pH 7 with a saturated aqueous sodium bicarbonate. After stirring for 15 minutes, the mixture was diluted with ethyl acetate and filtered through a pad of Celite. The organic layer was separated, washed with brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel (10 g) eluting with a mixture of benzene and acetone (5:1). Further purification on a silica gel (10 g) eluting with 10-20% ethyl acetate in dichloromethane) afforded methyl 2-[(3R,4R)-4-[2-(methoxycarbonylmethyl)allyl]-2-oxo-3-phthalimidoazetidin-1-yl]-3-methylbut-2-enoate (483 mg) as an oil.

Workup

  1. filtrationfiltered through a pad of Celite
  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 (10 g)
  7. washeluting with a mixture of benzene and acetone (5:1)
  8. customFurther purification on a silica gel (10 g)
  9. washeluting with 10-20% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-c9c0806ce4ae472a9afe53ac80ca8f8d
Source dataset
uspto-grants-1985_09
Patent number
US04539152

Reaction notes

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