Pyridine → (2S,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid

HRID 851631Notes

Reaction equation

HRID 851631 reaction equation
C([N+](CCCC)(CCCC)CCCC)CCC.C1(CC([NH:27][C@H:28]2[C@H:31]([CH3:32])[N:30]([S:33]([O-:36])(=[O:35])=[O:34])[C:29]2=[O:37])=O)C=CC=CC=1.N1C=CC=CC=1.C(Cl)(Cl)=O.FC(F)(F)C(O)=O>C(Cl)Cl.C1C=CC=CC=1.CO>[NH2:27][C@H:28]1[C@H:31]([CH3:32])[N:30]([S:33]([OH:36])(=[O:34])=[O:35])[C:29]1=[O:37]

Participants

8

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 6422Trifluoroacetic acidHCID 131713000(3S-trans)-4-methyl-2-oxo-3-(phenylacetylamino)-1-azetidinesulfonic acid, tetrabutylammonium salt

Product 1

HCID 133361(2S,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acidYield 34%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

(3S-trans)-3-[(Phenylacetyl)amino]-4-methyl-2-oxo-1-azetidinesulfonic acid, tetra-n-butylammonium salt (3.79 g) is dissolved in 70 ml of methylene chloride, cooled to -15° C. and 2.3 ml of pyridine is added. The cold mixture is treated with 5.8 ml of a 12% mixture of phosgene in benzene and stirred at -10° C. for 90 minutes. Methanol (35 ml) is added and the mixture is stirred for 30 minutes followed by the addition of 1.62 ml of trifluoroacetic acid. The reaction mixture is allowed to warm to room temperature and stirred for 16 hours. The precipitated material is collected by filtration, washed with methylene chloride and dried to yield 0.43 g of the title compound.

Workup

  1. stirringthe mixture is stirred for 30 minutes
  2. temperatureto warm to room temperature
  3. stirringstirred for 16 hours
  4. filtrationThe precipitated material is collected by filtration
  5. washwashed with methylene chloride
  6. customdried

Sources & evidence

ORD record
ord-05a6839c0e69449b9369abec182dd6e7
Source dataset
uspto-grants-1983_05
Patent number
US04386034

Reaction notes

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