Reaktion #44947

ord-e12423b6c0cc4975b07fb854a3c9a2cd

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 51.7%

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 methyl ketone

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 40 ml by vacuum distillation
3
workup.WAITafter standing for 15 hours
4
Filtrationthe crystalline product was filtered
5
Waschenwashed with cooled water (10 ml)
6
SonstigeThe product was then dried in an air
7
Sonstigeat RT

Vorschrift

Pseudomonic acid (10 g) was dissolved in isobutyl methyl ketone (120 ml). Calcium oxide (0.57 g) was suspended in water (68 ml), and added to the solution of pseudomonic acid. The mixture was stirred for one hour, and the phases were separated. The volume of the aqueous phase was reduced to 40 ml by vacuum distillation. The mixture was cooled to 5° C., and after standing for 15 hours, the crystalline product was filtered and washed with cooled water (10 ml). The product was then dried in an air circulated oven at RT. Mupirocin calcium dihydrate (3.7 g, 35%) was obtained.

Quelle

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