Réaction #44956

ord-60044640ac4f49cfa96a7c565ef0c340

Équation de réaction

C/C(=C\C(=O)OCCCCCCCCC(=O)O)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O)[C@H]1O
Pseudomonic acid
[Ca+2].[O-2]
Calcium oxide
O
Water
→
C/C(=C\C(=O)OCCCCCCCCC(=O)[O-])C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O)[C@H]1O.C/C(=C\C(=O)OCCCCCCCCC(=O)[O-])C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O)[C@H]1O.[Ca+2]
product
Rendement 87.7%
C/C(=C\C(=O)OCCCCCCCCC(=O)[O-])C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O)[C@H]1O.C/C(=C\C(=O)OCCCCCCCCC(=O)[O-])C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O)[C@H]1O.[Ca+2]
Mupirocin Calcium
Rendement 87.7%

Réactifs

C/C(=C\C(=O)OCCCCCCCCC(=O)O)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O)[C@H]1O
Pseudomonic acid
[Ca+2].[O-2]
Calcium oxide
O
Water

Réactifs

Aucun

Solvants

CO.O
methanol water

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    FiltrationThe solution was filtered
  2. 2
    Autrethe methanol was evaporated from the filtrate at reduced pressure
  3. 3
    Autreto give a final volume of 30 ml
  4. 4
    Autredried

Mode opératoire

Pseudomonic acid (10.01 g, 20 mmole) was dissolved in a mixture of methanol/water (50 ml and 36 ml). Calcium oxide (0.78 g, 14 mmole) was added portionwise to the mixture and was stirred for 1 h. The solution was filtered, and the methanol was evaporated from the filtrate at reduced pressure to give a final volume of 30 ml. Water (20 ml) was added to the solution. Then the solution was freeze dried to obtain 9.11 grams of product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07737177B2uspto-grants-2010_06