1,4-Dioxane → HCID 12817546, compound

HRID 1105781Notes

Reaction equation

HRID 1105781 reaction equation
[N+:1]([C:4]1[CH:38]=[CH:37][C:7]([CH2:8][O:9][C:10]([C@@H:12]2[N:16]3[C:17](=[O:33])[C@@H:18]([NH:19][C:20]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=4)=[O:21])[C@H:15]3[S@@:14](=O)[C:13]2([CH3:36])[CH3:35])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].ClC(Cl)(Cl)C[N:42]=[C:43]=[O:44].[O:47]1CCOCC1>>[N+:1]([C:4]1[CH:38]=[CH:37][C:7]([CH2:8][O:9][C:10]([C@@H:12]2[N:16]3[C:17](=[O:33])[C@@H:18]([NH:19][C:20]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=4)=[O:21])[C@H:15]3[S:14][C@:13]2([CH2:36][O:47][C:43](=[O:44])[NH2:42])[CH3:35])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 20344328HCID 20344328, compoundHCID 57307839HCID 57307839, compound

Product 1

HCID 12817546HCID 12817546, compound

Procedure

A mixture of (1S,3S,5R,6R) 6-(4-nitrobenzyloxycarbonyl)amino-2,2-dimethylpenam-3-carboxylic acid-oxide p-nitrobenzyl ester (8.19 g, 15.0 mmol), trichloroethyl isocyanate (5.0 ml, 7.9 g, 42 mmol) and dioxane (75 ml) was refluxed under nitrogen for 3.5 hours and concentrated in vacuo to a light brown oil. The oil was stirred with warm methanol (150 ml) for 0.5 hour and the solution was decanted from a small amount of dark residue. The methanol solution was adjusted to pH 7.4 with 5% sodium bicarbonate and held at pH 7.4-7.5 with 3% sulfuric acid during a 2.0 hour stirring period. The mixture was then distributed between methylene chloride (250 ml) and water (100 ml). The organic layer was washed with water (100 ml), combined with a CH2Cl2 back-extract (100 ml), dried (4A molecular sieve), polish filtered, and concentrated in vacuo to a light brown oil.

Workup

  1. temperaturewas refluxed under nitrogen for 3.5 hours
  2. concentrationconcentrated in vacuo to a light brown oil
  3. customthe solution was decanted from a small amount of dark residue
  4. waitheld at pH 7.4-7.5 with 3% sulfuric acid during a 2.0 hour
  5. stirringstirring period
  6. washThe organic layer was washed with water (100 ml)
  7. extractionback-extract (100 ml)
  8. dry with materialdried (4A molecular sieve), polish
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo to a light brown oil

Sources & evidence

ORD record
ord-12544d562f354ff397fda10a1ec9fb8e
Source dataset
uspto-grants-1982_01
Patent number
US04310459

Reaction notes

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