Mupirocin → Mupirocin Calcium

HRID 16670

Reaction equation

HRID 16670 reaction equation
[CH3:1][C@@H:2]([C@@H:33]([OH:35])[CH3:34])[C@@H:3]1[O:5][C@H:4]1[CH2:6][C@@H:7]1[C@@H:12]([OH:13])[C@@H:11]([OH:14])[C@H:10]([CH2:15]/[C:16](/[CH3:32])=[CH:17]/[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:19])[O:9][CH2:8]1.[Ca:36].C(C(CCCC)C([O-])=[O:41])C>C(OCC)(=O)C.O>[CH3:1][C@H:2]([C@H:3]1[C@H:4]([CH2:6][C@H:7]2[CH2:8][O:9][C@@H:10]([CH2:15]/[C:16](/[CH3:32])=[CH:17]/[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O-:31])=[O:30])=[O:19])[C@H:11]([OH:14])[C@@H:12]2[OH:13])[O:5]1)[C@H:33]([CH3:34])[OH:35].[CH3:1][C@H:2]([C@H:3]1[C@H:4]([CH2:6][C@H:7]2[CH2:8][O:9][C@@H:10]([CH2:15]/[C:16](/[CH3:32])=[CH:17]/[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O-:31])=[O:30])=[O:19])[C@H:11]([OH:14])[C@@H:12]2[OH:13])[O:5]1)[C@H:33]([CH3:34])[OH:35].[OH2:41].[OH2:5].[Ca+2:36]

Participants

5

Reactant 2

HCID 446596Mupirocin2×HCID 1317281822-Ethylhexanoate calcium2×

Product 1

HCID 5282317Mupirocin Calcium

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

Pseudomonic acid (10.00 g, 20 mmole) was dissolved in 100 ml of ethyl acetate at 40° C. Calcium-2-ethyl-hexanoate (3.32 g, 10 mmole) was suspended in 25 ml of water. The solution of pseudomonic acid was added to the calcium-2-ethyl-hexanoate suspension, and the resulting two phases system were stirred for 14 hours. The two phases were then separated, and any traces of ethyl acetate was evaporated from the aqueous phase. The aqueous mupirocin calcium suspension was cooled in the refrigerator to 5° C. and precipitated. The solid mupirocin calcium dihydrate was subsequently filtered, washed with 10 ml water and dried under vacuum at 35° C. for 14 hours. The mass of the product was 7.82 grams.

Workup

  1. customThe two phases were then separated
  2. customany traces of ethyl acetate was evaporated from the aqueous phase
  3. customprecipitated
  4. filtrationThe solid mupirocin calcium dihydrate was subsequently filtered
  5. washwashed with 10 ml water
  6. customdried under vacuum at 35° C. for 14 hours

Sources & evidence

ORD record
ord-8b86fee6ff1f407db918207bb3e49a73
Source dataset
uspto-grants-2010_06
Patent number
US07737177B2

Linked notes

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