Triphenylphosphine → HCID 22812921, compound

HRID 224551Notes

Reaction equation

HRID 224551 reaction equation
[CH2:1]([O:5][C@H:6]1[N:9]([CH:10](Cl)[C:11]([O:13][CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C:8](=[O:28])[C@@H:7]1[NH:29][C:30](=[O:38])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:2]([CH3:4])=[O:3].[C:39]1([P:45]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:1]([O:5][C@H:6]1[N:9]([C:10](=[P:45]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:11]([O:13][CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C:8](=[O:28])[C@@H:7]1[NH:29][C:30](=[O:38])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:2]([CH3:4])=[O:3]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 22812919HCID 22812919, compound

Product 1

HCID 22812921HCID 22812921, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude diphenylmethyl α-[4(R)-acetonyloxy-3(R)-phenylacetamido-2-oxo-azetidin-1-yl]-α-chloroacetate (2.251 g) in anhydrous methylene-chloride (20 ml) is added triphenylphosphine (1.50 g), and the mixture is refluxed for 4 hours under nitrogen atmosphere. The reaction mixture is poured into ice water, mixed with 5% aqueous solution of sodium hydrogen carbonate (20 ml), and extracted with methylene chloride. The organic layer is washed with water, dried over sodium sulfate, and evaporated under reduced pressure. Purification of the residue by chromatography over silica gel containing 10% water (100 g) using a mixture of benzene and ethyl acetate (1:2) as eluting solvent gives the product.

Workup

  1. temperaturethe mixture is refluxed for 4 hours under nitrogen atmosphere
  2. extractionextracted with methylene chloride
  3. washThe organic layer is washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customPurification of the residue by chromatography over silica gel containing 10% water (100 g)
  7. additiona mixture of benzene and ethyl acetate (1:2)
  8. washas eluting solvent
  9. customgives the product

Sources & evidence

ORD record
ord-46dddbd01d1e4551b7695e73b736e35b
Source dataset
uspto-grants-1980_11
Patent number
US04233216

Reaction notes

Loading…