Reaktion #44952

ord-66b500ba0ee0474fa99c23326d5aba2f

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

Calcium oxide

$C/C(=C\C(=O)OCCCCCCCCC(=O)O)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O)[C@H]1O$

pseudomonic acid

→

$C/C(=C\C(=O)OCCCCCCCCC(=O)[O-])C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O)[C@H]1O.C/C(=C\C(=O)OCCCCCCCCC(=O)[O-])C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O)[C@H]1O.O.O.[Ca+2]$

Mupirocin calcium dihydrate

Ausbeute 62.0%

Edukte

$C/C(=C\C(=O)OCCCCCCCCC(=O)O)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O)[C@H]1O$

Pseudomonic acid

Calcium oxide

$C/C(=C\C(=O)OCCCCCCCCC(=O)O)C[C@@H]1OC[C@H](C[C@@H]2O[C@H]2[C@@H](C)[C@H](C)O)[C@@H](O)[C@H]1O$

pseudomonic acid

Reagenzien

Keine

Lösungsmittel

isobutyl acetate

water

Reaktionsbedingungen

Temperatur

5°CELSIUS

Detaillierte Bedingungen

See reaction.notes.procedure_details.

Aufarbeitung

1
Sonstigethe phases were separated
2
workup.DISTILLATIONThe volume of the aqueous phase was reduced to 15 ml by vacuum distillation
3
workup.STIRRINGAfter stirring for 2 hours
4
Filtrationthe crystalline product was filtered
5
Waschenwashed with cooled water (5 ml)
6
SonstigeThe product was dried in an air
7
Sonstigeat RT

Vorschrift

Pseudomonic acid was dissolved in isobutyl acetate (130 ml). Calcium oxide (0.29 g) was suspended in water (32 ml) and added to the solution of pseudomonic acid. The mixture was stirred for 2 hours, and the phases were separated. The volume of the aqueous phase was reduced to 15 ml by vacuum distillation. The mixture was cooled to 5° C. After stirring for 2 hours, the crystalline product was filtered and washed with cooled water (5 ml). The product was dried in an air circulated oven at RT. Mupirocin calcium dihydrate (3.3 g, 62%) was obtained.

Quelle

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