Formic Acid → HCID 13478225, compound

HRID 371235Notes

Reaction equation

HRID 371235 reaction equation
[C:1]([C@@H:3]1[NH:6][C:5](=[O:7])[C@H:4]1[NH:8]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[CH:2].N1C=CC=CC=1.[S:34](=[O:37])(=[O:36])=[O:35].C(O)=O>ClCCl>[NH2:8][C@H:4]1[C@H:3]([C:1]#[CH:2])[N:6]([S:34]([OH:37])(=[O:36])=[O:35])[C:5]1=[O:7]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 1049PyridineHCID 24682Sulfur trioxideHCID 15058003HCID 15058003, compound

Product 1

HCID 13478225HCID 13478225, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-(trans)-4-ethynyl-2-oxo-3-[(triphenylmethyl)amino]azetidine (404 mg) and 560 mg of a complex of pyridine and sulfur trioxide are added to a 25 ml flask. After the flask is flushed with nitrogen, 4.0 ml of dry pyridine is added and the mixture is heated at 80°-85° C. for 3 hours. The mixture is added to a rapidly stirred mixture of 4.0 ml of concentrated hydrochloric acid, 50 ml of water, and 50 ml of ethyl acetate. The pH is adjusted to 3.15 with sodium carbonate. The water layer is separated and extracted once with ethyl acetate. The combined organic layer is washed once with saturated aqueous sodium chloride, dried over sodium sulfate and filtered. Solvent removal in vacuo gives a foam which is taken up in 10 ml of dichloromethane. Formic acid (98%, 8 ml) is added, and after 15 minutes the mixture is concentrated to 4 ml and 10 ml of dichloromethane is added to give a solid suspended in solution. Filtration gives 100 mg of the title compound as a solid (obvious discoloration with melting >180° C.).

Workup

  1. customAfter the flask is flushed with nitrogen, 4.0 ml of dry pyridine
  2. additionis added
  3. temperaturethe mixture is heated at 80°-85° C. for 3 hours
  4. additionThe mixture is added to a rapidly stirred mixture of 4.0 ml of concentrated hydrochloric acid, 50 ml of water, and 50 ml of ethyl acetate
  5. customThe water layer is separated
  6. extractionextracted once with ethyl acetate
  7. washThe combined organic layer is washed once with saturated aqueous sodium chloride
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customSolvent removal in vacuo
  11. customgives a foam which
  12. concentrationafter 15 minutes the mixture is concentrated to 4 ml and 10 ml of dichloromethane
  13. additionis added
  14. customto give a solid
  15. filtrationFiltration

Sources & evidence

ORD record
ord-9c4bc837e41941968418eac969016fc1
Source dataset
uspto-grants-1985_07
Patent number
US04529698

Reaction notes

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