تفاعل #44951

ord-f9f37bcdc3464a7d9848ba524564d05b

معادلة التفاعل

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

المتفاعلات

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

الكواشف

لا شيء

المذيبات

O
water
O
water
CC(=O)CC(C)C
isobutyl methyl ketone

ظروف التفاعل

درجة الحرارة
5°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىto obtain a solution
  2. 2
    أخرىThe two phases were then separated
  3. 3
    workup.ADDITIONisobutyl methyl ketone (25 ml) was added to the aqueous phase
  4. 4
    workup.STIRRINGstirred for 10 minutes
  5. 5
    أخرىThe two resulting phases were separated
  6. 6
    أخرىany traces of isobutyl methyl ketone was evaporated from the aqueous phase
  7. 7
    ترشيحThe solid mupirocin calcium dihydrate was filtered
  8. 8
    غسيلwashed with water (20 ml)
  9. 9
    أخرىdried under vacuum at 35° C. for 14 hours

الإجراء التجريبي

Pseudomonic acid (10.00 g, 20 mmole) was dissolved in isobutyl methyl ketone (100 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 were stirred for 24 hours. The two phases were then separated, isobutyl methyl ketone (25 ml) was added to the aqueous phase, and stirred for 10 minutes. The two resulting phases were separated, and any traces of isobutyl methyl ketone was evaporated from the aqueous phase. The aqueous mupirocin calcium suspension was cooled in a 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 7.95 grams. Assay 97.72%, water: 3.45%.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07737177B2uspto-grants-2010_06