Dichloromethane → (trans)-3-Amino-4-ethyl-2-oxo-1-azetidinesulfonic acid

HRID 867653Notes

Reaction equation

HRID 867653 reaction equation
C([N+](CCCC)(CCCC)CCCC)CCC.C(OC([NH:25][C@H:26]1[C@H:29]([CH2:30][CH3:31])[N:28]([S:32]([O-:35])(=[O:34])=[O:33])[C:27]1=[O:36])=O)(C)(C)C.ClCCl>C(O)=O>[NH2:25][C@H:26]1[C@H:29]([CH2:30][CH3:31])[N:28]([S:32]([OH:35])(=[O:33])=[O:34])[C:27]1=[O:36]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 131714274(trans)-3-t-Butoxycarbonylamino-4-ethyl-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt

Product 1

HCID 13575528(trans)-3-Amino-4-ethyl-2-oxo-1-azetidinesulfonic acidYield 34.7%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

(trans)-3-t-Butoxycarbonylamino-4-ethyl-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt (6.75 g) in 40 ml of 98% formic acid is stirred for 3 hours at ambient temperature. Dichloromethane (60 ml) is added and the mixture is refrigerated for about 16 hours. The resulting precipitate is separated by filtration and then dried in vacuo to yield 0.85 g of the title compound, melting point 185° C., dec.

Workup

  1. customThe resulting precipitate is separated by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-f0bb8e6b1f844640b2388124c3912948
Source dataset
uspto-grants-1988_10
Patent number
US04775670

Reaction notes

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