Water → Butyl cis-3-azido-4-oxo-2-azetidinecarboxylate

HRID 1862885

Reaction equation

HRID 1862885 reaction equation
C([N:14]1[C:17](=[O:18])[C@H:16]([N:19]=[N+:20]=[N-:21])[C@@H:15]1[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:23])(C1C=CC=CC=1)C1C=CC=CC=1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].O.O.O.O.O.O.O.O.O.O.O.O.P(O)([O-])([O-])=O.[Na+].[Na+].O>C(#N)C>[N:19]([C@H:16]1[C:17](=[O:18])[NH:14][C@H:15]1[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:23])=[N+:20]=[N-:21]

Participants

6

Reactant 4

HCID 962WaterHCID 24412Potassium PersulfateHCID 61456Phosphoric acid, disodium salt, dodecahydrateHCID 86735452Butyl cis-1-benzhydryl-3-azido-4-oxo-2-azetidine carboxylate

Product 1

HCID 86735451Butyl cis-3-azido-4-oxo-2-azetidinecarboxylateYield 175.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 200 mg (0.529 mmole) of butyl cis-1-benzhydryl-3-azido-4-oxo-2-azetidine carboxylate, 473 mg (1.75 mmole) of potassium persulfate, 307 mg (0.858 mmole) of disodium phosphate dodecahydrate, 9.2 ml of water and 8.4 ml of acetonitrile was thoroughly degassed with argon and then heated to 80°-85° C. under argon for three hours. The reaction mixture was cooled and the acetonitrile removed on the rotary evaporator. The aqueous residue was saturated with solid sodium chloride and extracted three times with ethyl acetate. The combined organic extractions were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 197 mg of crude material. This material was chromatographed on ten grams of 70-230 mesh silica gel and 31 mg (28%) of the desired product, a light yellow foam was eluted with 20% EtOAc in benzene. tlc: silica gel GF; 20% ethylacetate benzene, R.f.=0.15.

Workup

  1. customwas thoroughly degassed with argon
  2. temperatureheated to 80°-85° C. under argon for three hours
  3. temperatureThe reaction mixture was cooled
  4. customthe acetonitrile removed on the rotary evaporator
  5. extractionextracted three times with ethyl acetate
  6. extractionThe combined organic extractions
  7. washwere washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-58fa06cdee7449099350a191e6454cc7
Source dataset
uspto-grants-1979_09
Patent number
US04166816

Linked notes

Loading…