Pyridine → HCID 13232644, compound

HRID 1788797Notes

Reaction equation

HRID 1788797 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.[NH2:12][C@H:13]1[CH:16]([C:17]#[N:18])[NH:15][C:14]1=[O:19].N1C=CC=CC=1.[C:26]1([CH2:32][C:33](Cl)=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl.O>[C:17]([C@H:16]1[NH:15][C:14](=[O:19])[C@H:13]1[NH:12][C:33](=[O:34])[CH2:32][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)#[N:18]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 7679Phenylacetyl chlorideHCID 13232641HCID 13232641, compound

Product 1

HCID 13232644HCID 13232644, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

In 100 ml of methylene chloride were dissolved under ice-cooling 5 g of p-toluenesulfonate of (3S, 4RS)-3-amino-4-cyano-2-azetidinone and 4.2 g of pyridine. To the solution was added 3 g of phenylacetyl chloride. The mixture was stirred at room temperature (about 25° C.) for ten minutes, which was shaken with water. The organic layer was separated and dried on anhydrous magnesium sulfate, then concentrated under reduced pressure. The concentrate was purified on a silicagel column chromatography [ethyl acetate: n-hexane (2:1)] to yield 1.16 g of (3S, 4S)-4-cyano-3-phenylacetamido-2-azetidinone (A) and subsequently 0.84 g of a corresponding (3S-4R)-derivative (B).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried on anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe concentrate was purified on a silicagel column chromatography [ethyl acetate: n-hexane (2:1)]

Sources & evidence

ORD record
ord-a8d6626d43bf43faa9840510eb71c657
Source dataset
uspto-grants-1987_08
Patent number
US04684724

Reaction notes

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