Reaktion #44953

ord-579cddfbb4a741998b646c1cbd395ffd

Reaktionsgleichung

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
[K+].[OH-]
potassium hydroxide
[Ca+2].[Cl-].[Cl-]
calcium chloride
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]
final product
Ausbeute 93.3%
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
Ausbeute 93.3%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe solution was then filtered
  2. 2
    Sonstigeto remove potassium chloride (0.60 g)
  3. 3
    SonstigeThe methanol was then evaporated at reduced pressure
  4. 4
    Sonstigeto give a solid, white foam
  5. 5
    SonstigeThe product was dried for 12 hours at 45° C. under vacuum

Vorschrift

Pseudomonic acid (5.00 g, 10 mmole) was dissolved in methanol (5.5 ml), methanolic solution of potassium hydroxide (0.56 g, 10 mmole potassium hydroxide and 4 ml methanol) and methanolic solution of calcium chloride (0.56 g, 5.0 mmole calcium chloride and 5 ml methanol) were added to the mixture. The mixture was stirred for 1 hour. The solution was then filtered to remove potassium chloride (0.60 g). The methanol was then evaporated at reduced pressure to give a solid, white foam. The product was dried for 12 hours at 45° C. under vacuum to obtain 4.85 grams of final product. Assay: 95.9%, Water: 2.23% [total impurity: 3.19%, highest impurity: 1.23%-different method than assay], melting point: 85 to 89° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07737177B2uspto-grants-2010_06