(3S-trans)-3-[(t-butoxycarbonyl)amino]-4-methyl-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt → (2S,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid

HRID 851629Notes

Reaction equation

HRID 851629 reaction equation
C([N+](CCCC)(CCCC)CCCC)CCC.C(OC([NH:25][C@H:26]1[C@H:29]([CH3:30])[N:28]([S:31]([O-:34])(=[O:33])=[O:32])[C:27]1=[O:35])=O)(C)(C)C>C(O)=O.C(Cl)Cl>[NH2:25][C@H:26]1[C@H:29]([CH3:30])[N:28]([S:31]([OH:34])(=[O:32])=[O:33])[C:27]1=[O:35]

Participants

4

Reactant 1

HCID 13146192(3S-trans)-3-[(t-butoxycarbonyl)amino]-4-methyl-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt

Product 1

HCID 133361(2S,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

(3S-trans)-3-[(t-Butoxycarbonyl)amino]-4-methyl-2-oxo-1-azetidinesulfonic acid tetra-n-butylammonium salt (6.3 g) is dissolved in 30 ml of 97% formic acid and stirred for 5 hours during which time a precipitate forms. The slurry is diluted with 30 ml of methylene chloride and filtered. The solids are further washed with methylene chloride and dried to yield 1.53 g of analytically pure product [αD21 =-41.0[c=1, water].

Workup

  1. filtrationfiltered
  2. washThe solids are further washed with methylene chloride
  3. customdried
  4. customto yield 1.53 g of analytically pure product [αD21 =-41.0[c=1, water]

Sources & evidence

ORD record
ord-4366f724c1d84131abd95e8859108e28
Source dataset
uspto-grants-1983_05
Patent number
US04386034

Reaction notes

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