Réaction #318719

ord-46fcdc8875474d52a768dad769d5c703

Équation de réaction

C1CCC([NH2+]C2CCCCC2)CC1
dicyclohexylammonium
CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccccc3)[C@H]2SC1(C)C.Cl
bacampicillin hydrochloride
→
CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccccc3)[C@H]2SC1(C)C
desired compound
Rendement 118.7%
CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccccc3)[C@H]2SC1(C)C
Bacampicillin
Rendement 118.7%

Réactifs

C1CCC([NH2+]C2CCCCC2)CC1
dicyclohexylammonium
CCOC(=O)OC(C)OC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccccc3)[C@H]2SC1(C)C.Cl
bacampicillin hydrochloride

Réactifs

Aucun

Solvants

O
water
O
water

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Filtrationthe crystals were filtered off
  2. 2
    Lavagewashed with water (2×150 ml)
  3. 3
    Autredried

Mode opératoire

To a stirred suspension of dicyclohexylammonium 6β-bromopenicillanate (46.15 g, 100 mmol; as prepared in Example 3c, 1st crop) in water (800 ml) was added dropwise during 75 minutes a solution of bacampicillin hydrochloride (60.24 g, 120 mmol) in water (800 ml). After stirring for an additional 2 hours, the crystals were filtered off, washed with water (2×150 ml) followed by hexane (2×250 ml), and dried to yield 66.3 g (85.8%) of the desired compound.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04847266uspto-grants-1989_07