Water → Bactroban

HRID 16678

Reaction equation

HRID 16678 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].[Ca+2:37].O>CO.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].[Ca+2:37]

Participants

5

Reactant 3

HCID 962WaterHCID 446596MupirocinHCID 6850728Calciumoxide

Product 1

HCID 6435927BactrobanYield 87.7%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Pseudomonic acid (10.01 g, 20 mmole) was dissolved in a mixture of methanol/water (50 ml and 36 ml). Calcium oxide (0.78 g, 14 mmole) was added portionwise to the mixture and was stirred for 1 h. The solution was filtered, and the methanol was evaporated from the filtrate at reduced pressure to give a final volume of 30 ml. Water (20 ml) was added to the solution. Then the solution was freeze dried to obtain 9.11 grams of product.

Workup

  1. filtrationThe solution was filtered
  2. customthe methanol was evaporated from the filtrate at reduced pressure
  3. customto give a final volume of 30 ml
  4. customdried

Sources & evidence

ORD record
ord-60044640ac4f49cfa96a7c565ef0c340
Source dataset
uspto-grants-2010_06
Patent number
US07737177B2

Linked notes

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