Réaction #2383785

ord-13df5704c1e6473eb91893e0eeb1dd5b

Équation de réaction

CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O
6-aminopenicillanic acid
[K+].[O]=[Mn](=[O])(=[O])[O-]
potassium permanganate
O=S(=O)(O)O
sulfuric acid
O=S([O-])O.[Na+]
sodium bisulfite
N
ammonia
→
CC1(C)[C@H](C(=O)O)N2C(=O)[C@H](N)[C@H]2S1(=O)=O
desired product
Rendement 78.0%
CC1(C)[C@H](C(=O)O)N2C(=O)[C@H](N)[C@H]2S1(=O)=O
(2S,5R,6S)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo-[3.2.0]heptane-2-carboxylic acid 4,4-dioxide
Rendement 78.0%

Réactifs

CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O
6-aminopenicillanic acid
[K+].[O]=[Mn](=[O])(=[O])[O-]
potassium permanganate
O=S(=O)(O)O
sulfuric acid
O=S([O-])O.[Na+]
sodium bisulfite
—
sulfone
N
ammonia

Réactifs

Aucun

Solvants

O
water
CC#N
acetonitrile
O
water

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONwas added
  2. 2
    workup.ADDITIONAt the end of the addition
  3. 3
    Autrewas passed through the solution at 0° C. until pH 3, at which time
  4. 4
    Autreprecipitated
  5. 5
    FiltrationThe solid was filtered
  6. 6
    Lavagewashed with acetone
  7. 7
    Autredried in vacuo

Mode opératoire

To a 0° C. solution of 6-aminopenicillanic acid (10.0 g, 0.046 mol) in a mixture of water (32 mL) and acetonitrile(48 mL) was added, dropwise, a solution containing potassium permanganate (9.6 g, 0.061 mol) and concentrated sulfuric acid (6 mL) in water (120 mL). At the end of the addition, a 50% aqueous sodium bisulfite solution was added, dropwise, to the reaction mixture until a clear solution was observed. Anhydrous ammonia gas was passed through the solution at 0° C. until pH 3, at which time the sulfone product precipitated. The solid was filtered, washed with acetone and dried in vacuo to obtain 9.0 g(78%) of the desired product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US06489316B2uspto-grants-2002_12