Reaction #44950

ord-67e2007edfc94f4da80775a7d2f03cf0

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
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
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

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

Reagents

None

Solvents

O
water
O
water
COC(C)(C)C
methyl tertbutyl ether

Conditions

Temperature
5°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherto obtain a solution
  2. 2
    OtherThe two phases were separated
  3. 3
    workup.ADDITION50 ml methyl tertbutyl ether was added to the aqueous phase
  4. 4
    workup.STIRRINGstirred for 10 minutes
  5. 5
    OtherThe two resulting phases were separated
  6. 6
    Otherthe methyl tertbutyl ether was evaporated from the aqueous phase
  7. 7
    FiltrationThe solid mupirocin calcium dihydrate was filtered
  8. 8
    Washwashed with water (20 ml)
  9. 9
    Otherdried under vacuum at 35° C. for 14 hours

Procedure

Pseudomonic acid (10.00 g, 20 mmole) was dissolved in methyl tertbutyl ether (180 ml) at 40° C. Calcium-2-ethyl-hexanoate (3.32 g, 10 mmole) was suspended in water (50 ml). (It is possible to obtain a solution by using a larger amount of water or an alcohol/water mixture). The solution of pseudomonic acid was added to the calcium-2-ethyl-hexanoate suspension, and the two phase system was stirred for 24 hours. The two phases were separated, 50 ml methyl tertbutyl ether was added to the aqueous phase and stirred for 10 minutes. The two resulting phases were separated, and the methyl tertbutyl ether was evaporated from the aqueous phase. The aqueous mupirocin calcium suspension was cooled in the refrigerator at 5° C. The solid mupirocin calcium dihydrate was filtered, washed with water (20 ml) and dried under vacuum at 35° C. for 14 hours. The mass of product was 8.65 grams. Assay: 95.68%, water: 3.48%

Source

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