Mupirocin → Mupirocin Calcium

HRID 16671

Reaction equation

HRID 16671 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(OC)(C)(C)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 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
5 °C

Procedure

Pseudomonic acid (10.00 g, 20 mmole) was dissolved in methyl tertbutyl ether (150 ml) at 45° C. Calcium-2-ethyl-hexanoate (3.32 g, 10 mmole) was suspended in water (30 ml). 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 water (20 ml) and methyl tertbutyl ether (50 ml) was added to the aqueous phase, and was stirred for 10 minutes. The resulting two phases were separated, and any traces of methyl tertbutyl ether 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 20 ml water and dried under vacuum at 35° C. for 5 hours. The mass of product was 5.88 grams.

Workup

  1. customThe two phases were then separated
  2. additionwater (20 ml) and methyl tertbutyl ether (50 ml) was added to the aqueous phase
  3. stirringwas stirred for 10 minutes
  4. customThe resulting two phases were separated
  5. customany traces of methyl tertbutyl ether was evaporated from the aqueous phase
  6. filtrationThe solid mupirocin calcium dihydrate was filtered
  7. washwashed with 20 ml water
  8. customdried under vacuum at 35° C. for 5 hours

Sources & evidence

ORD record
ord-0fc46a41f0614cc0a0e4d092de2ac044
Source dataset
uspto-grants-2010_06
Patent number
US07737177B2

Linked notes

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