Reaction #44954

ord-c43bc1f15fb047039a3f2047a022f421

Reaction equation

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

Pseudomonic acid

potassium hydroxide

calcium chloride

→

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

Mupirocin Calcium

Reactants

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

Pseudomonic acid

potassium hydroxide

calcium chloride

Reagents

None

Solvents

ethanol

Conditions

Detailed conditions

See reaction.notes.procedure_details.

Workup

1
Filtrationthe solution was filtered
2
Otherto remove potassium chloride (0.51 g)
3
OtherThe ethanol was subsequently evaporated at reduced pressure
4
Otherto give a solid, white foam
5
OtherThe product was dried for 12 hours at 45° C. under vacuum

Procedure

Pseudomonic acid (5.00 g, 10 mmole) was dissolved in ethanol (20 ml), ethanolic solution of potassium hydroxide (0.56 g, 10 mmole potassium hydroxide and 10 ml ethanol) and ethanolic solution of calcium chloride (0.56 g, 5.0 mmole calcium chloride and 10 ml ethanol) were added to the mixture. The mixture was stirred for 1 hour and the solution was filtered to remove potassium chloride (0.51 g). The ethanol was subsequently evaporated at reduced pressure to give a solid, white foam. The product was dried for 12 hours at 45° C. under vacuum. The product had a mass of 4.38 grams. Assay: 99.1%, water: 2.36% [total impurity: 2.44%, highest impurity: 1.10% different method than the assay].

Source

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