Reaktion #44948

ord-8b86fee6ff1f407db918207bb3e49a73

Reaktionsgleichung

CCCCC(CC)C(=O)[O-].[Ca]
Calcium 2-ethyl-hexanoate
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
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
CCCCC(CC)C(=O)[O-].[Ca]
calcium 2-ethyl-hexanoate
→
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.O.O.[Ca+2]
Mupirocin Calcium Dihydrate

Edukte

CCCCC(CC)C(=O)[O-].[Ca]
Calcium 2-ethyl-hexanoate
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
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
CCCCC(CC)C(=O)[O-].[Ca]
calcium 2-ethyl-hexanoate

Reagenzien

Keine

Lösungsmittel

O
water
CCOC(C)=O
ethyl acetate

Reaktionsbedingungen

Temperatur
5°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe two phases were then separated
  2. 2
    Sonstigeany traces of ethyl acetate was evaporated from the aqueous phase
  3. 3
    Sonstigeprecipitated
  4. 4
    FiltrationThe solid mupirocin calcium dihydrate was subsequently filtered
  5. 5
    Waschenwashed with 10 ml water
  6. 6
    Sonstigedried under vacuum at 35° C. for 14 hours

Vorschrift

Pseudomonic acid (10.00 g, 20 mmole) was dissolved in 100 ml of ethyl acetate at 40° C. Calcium-2-ethyl-hexanoate (3.32 g, 10 mmole) was suspended in 25 ml of water. The solution of pseudomonic acid was added to the calcium-2-ethyl-hexanoate suspension, and the resulting two phases system were stirred for 14 hours. The two phases were then separated, and any traces of ethyl acetate was evaporated from the aqueous phase. The aqueous mupirocin calcium suspension was cooled in the refrigerator to 5° C. and precipitated. The solid mupirocin calcium dihydrate was subsequently filtered, washed with 10 ml water and dried under vacuum at 35° C. for 14 hours. The mass of the product was 7.82 grams.

Quelle

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