Bactroban → Mupirocin Calcium

HRID 16668

Reaction equation

HRID 16668 reaction equation
[CH3:1][C@H:2]([C@H:6]1[C@H:8]([CH2:9][C@H:10]2[CH2:15][O:14][C@@H:13]([CH2:16]/[C:17](/[CH3:33])=[CH:18]/[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O-:32])=[O:31])=[O:20])[C@H:12]([OH:34])[C@@H:11]2[OH:35])[O:7]1)[C@H:3]([CH3:5])[OH:4].[CH3:36][C@H:37]([C@H:41]1[C@H:43]([CH2:44][C@H:45]2[CH2:50][O:49][C@@H:48]([CH2:51]/[C:52](/[CH3:68])=[CH:53]/[C:54]([O:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][C:65]([O-:67])=[O:66])=[O:55])[C@H:47]([OH:69])[C@@H:46]2[OH:70])[O:42]1)[C@H:38]([CH3:40])[OH:39].[Ca+2:71]>O>[CH3:1][C@H:2]([C@H:6]1[C@H:8]([CH2:9][C@H:10]2[CH2:15][O:14][C@@H:13]([CH2:16]/[C:17](/[CH3:33])=[CH:18]/[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O-:32])=[O:31])=[O:20])[C@H:12]([OH:34])[C@@H:11]2[OH:35])[O:7]1)[C@H:3]([CH3:5])[OH:4].[CH3:36][C@H:37]([C@H:41]1[C@H:43]([CH2:44][C@H:45]2[CH2:50][O:49][C@@H:48]([CH2:51]/[C:52](/[CH3:68])=[CH:53]/[C:54]([O:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][C:65]([O-:67])=[O:66])=[O:55])[C@H:47]([OH:69])[C@@H:46]2[OH:70])[O:42]1)[C@H:38]([CH3:40])[OH:39].[OH2:4].[OH2:4].[Ca+2:71]

Participants

3

Reactant 1

HCID 6435927Bactroban2×

Product 1

HCID 5282317Mupirocin Calcium

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

Amorphous mupirocin calcium (20.00 g, 19.20 mmole) was added into water (20 ml) under stirring. The slurry was stirred for 0.5 hour, and then it was cooled to 5° C. The mupirocin calcium solution was allowed to crystallize for 16 h. The crystal slurry was diluted with 15 ml water, and the crystals were filtered and washed with water (5 ml). The product (17.1 g) was dried at 35° C. for 12 h.

Workup

  1. stirringThe slurry was stirred for 0.5 hour
  2. customto crystallize for 16 h
  3. additionThe crystal slurry was diluted with 15 ml water
  4. filtrationthe crystals were filtered
  5. washwashed with water (5 ml)
  6. dry with materialThe product (17.1 g) was dried at 35° C. for 12 h.

Sources & evidence

ORD record
ord-c603df2915db4aa49e683e2e9f3cc60b
Source dataset
uspto-grants-2010_06
Patent number
US07737177B2

Linked notes

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