Реакция #44952

ord-66b500ba0ee0474fa99c23326d5aba2f

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
[Ca+2].[O-2]
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
Выход 62.0%

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
[Ca+2].[O-2]
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

Реагенты

Нет

Растворители

CC(=O)OCC(C)C
isobutyl acetate
O
water

Условия реакции

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

Обработка

  1. 1
    Другоеthe phases were separated
  2. 2
    workup.DISTILLATIONThe volume of the aqueous phase was reduced to 15 ml by vacuum distillation
  3. 3
    workup.STIRRINGAfter stirring for 2 hours
  4. 4
    Фильтрацияthe crystalline product was filtered
  5. 5
    Промывкаwashed with cooled water (5 ml)
  6. 6
    ДругоеThe product was dried in an air
  7. 7
    Другоеat RT

Методика

Pseudomonic acid was dissolved in isobutyl acetate (130 ml). Calcium oxide (0.29 g) was suspended in water (32 ml) and added to the solution of pseudomonic acid. The mixture was stirred for 2 hours, and the phases were separated. The volume of the aqueous phase was reduced to 15 ml by vacuum distillation. The mixture was cooled to 5° C. After stirring for 2 hours, the crystalline product was filtered and washed with cooled water (5 ml). The product was dried in an air circulated oven at RT. Mupirocin calcium dihydrate (3.3 g, 62%) was obtained.

Источник

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