8-Hydroxyquinoline → (3S-trans)-2-Oxo-3-[[(phenylmethoxy)carbonyl]-amino]-4-methyl-1-azetidinesulfonic acid, 8-hydroxyquinolinium salt

HRID 279765Notes

Reaction equation

HRID 279765 reaction equation
C([N+](CCCC)(CCCC)CCCC)CCC.[O:18]=[C:19]1[C@@H:22]([NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[C@H:21]([CH3:34])[N:20]1[S:35]([O-:38])(=[O:37])=[O:36].[OH:39][C:40]1[CH:41]=[CH:42][CH:43]=[C:44]2[C:49]=1[N:48]=[CH:47][CH:46]=[CH:45]2>O.C(#N)C>[OH:39][C:40]1[CH:41]=[CH:42][CH:43]=[C:44]2[C:49]=1[NH+:48]=[CH:47][CH:46]=[CH:45]2.[O:18]=[C:19]1[C@@H:22]([NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[C@H:21]([CH3:34])[N:20]1[S:35]([O-:38])(=[O:36])=[O:37]

Participants

5

Reactant 2

HCID 19238-HydroxyquinolineHCID 13631608Tetrabutylammonium (2S,3S)-3-{[(benzyloxy)carbonyl]amino}-2-methyl-4-oxoazetidine-1-sulfonate

Product 1

HCID 131714652(3S-trans)-2-Oxo-3-[[(phenylmethoxy)carbonyl]-amino]-4-methyl-1-azetidinesulfonic acid, 8-hydroxyquinolinium saltYield 96.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(3S-trans)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-1-azetidinesulfonic acid, tetrabutylammonium salt (500 mg, 0.9 mmol) was dissolved in a mixture of water and acetonitrile. The solution was passed through an AGMP-50 ion-exchange resin column (H⊕ form, 7 ml, 1.7 meq/ml) eluting with water. The eluate was run into a flask containing 8-hydroxyquinoline (131 mg, 0.9 mmol). Acetonitrile was removed from the resulting solution under reduced pressure at <35° C. and the remaining aqueous solution was lyophilized yielding a solid. Trituration with ether and drying in vacuo afforded the desired product as a yellow powder (398 mg), melting point 61°-68° C.

Workup

  1. washeluting with water
  2. customThe eluate was run into a flask
  3. customAcetonitrile was removed from the resulting solution under reduced pressure at <35° C.
  4. customthe remaining aqueous solution was lyophilized yielding a solid
  5. dry with materialTrituration with ether and drying in vacuo

Sources & evidence

ORD record
ord-bd9e96b6c99a4a46a76c1c6dcacb3790
Source dataset
uspto-grants-1986_05
Patent number
US04587051

Reaction notes

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