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Mupirocin → Mupirocin Calcium

HRID 16669
Notes
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Reaction equation

HRID 16669 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.[O-2:36].[Ca+2:37]>CC(CC(C)C)=O.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].[OH2:36].[OH2:5].[Ca+2:37]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 446596Mupirocin2×HCID 6850728Calciumoxide

Product 1

HCID 5282317Mupirocin CalciumYield 51.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
5 °C

Procedure

Pseudomonic acid (10 g) was dissolved in isobutyl methyl ketone (120 ml). Calcium oxide (0.57 g) was suspended in water (68 ml), and added to the solution of pseudomonic acid. The mixture was stirred for one hour, and the phases were separated. The volume of the aqueous phase was reduced to 40 ml by vacuum distillation. The mixture was cooled to 5° C., and after standing for 15 hours, the crystalline product was filtered and washed with cooled water (10 ml). The product was then dried in an air circulated oven at RT. Mupirocin calcium dihydrate (3.7 g, 35%) was obtained.

Workup

  1. customthe phases were separated
  2. distillationThe volume of the aqueous phase was reduced to 40 ml by vacuum distillation
  3. waitafter standing for 15 hours
  4. filtrationthe crystalline product was filtered
  5. washwashed with cooled water (10 ml)
  6. customThe product was then dried in an air
  7. customat RT

Sources & evidence

ORD record
ord-e12423b6c0cc4975b07fb854a3c9a2cd
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737177B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes