Реакция #44950

ord-67e2007edfc94f4da80775a7d2f03cf0

Уравнение реакции

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

Реактанты

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

Реагенты

Нет

Растворители

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

Условия реакции

Температура
5°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Другоеto obtain a solution
  2. 2
    ДругоеThe 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
    ДругоеThe two resulting phases were separated
  6. 6
    Другоеthe methyl tertbutyl ether was evaporated from the aqueous phase
  7. 7
    ФильтрацияThe solid mupirocin calcium dihydrate was filtered
  8. 8
    Промывкаwashed with water (20 ml)
  9. 9
    Другоеdried under vacuum at 35° C. for 14 hours

Методика

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%

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07737177B2uspto-grants-2010_06