ChemicalBook CAS DataBase List RETAPAMULIN

RETAPAMULIN synthesis

3synthesis methods

Product Name:RETAPAMULIN
CAS Number:224452-66-8
Molecular formula:C30H47NO4S
Molecular Weight:517.76

Retapamulin, also known as SB-275833, is a newer topical agent of pleuromutilin class approved by the Food and Drug Administration for treatment of impetigo in children. It has been demonstrated to have low potential for the development of antibacterial resistance and a high degree of potency against poly drug resistant Gram-positive bacteria found in skin infections including Staphylococcus aureus strains. The drug is safe owing to low systemic absorption and has only minimal side-effect of local irritation at the site of application.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

ROUTE 8

ROUTE 9

ROUTE 10

Breen, Gary Francis; Forth, Michael Anthony; Kopelman, Susan Shumei Hu; Muller, Francis Xavier; Sanderson, Francis Dominic. Process for preparation of mutilin derivatives and their salts as antibacterial agents. Assignee Glaxo Group Limited, UK. WO 2005023257. (2005).

8-Azabicyclo[3.2.1]octane-3-thiol, 8-Methyl-, (3-exo)-

848130-83-6
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60924-38-1 Synthesis

2-[(Methylsulfonyl)oxy]acetic acid (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester

60924-38-1
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224452-66-8
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Yield:224452-66-8 80%

Reaction Conditions:

with triethylamine in 4-methyl-2-pentanone at 20 - 40; for 2 - 24 h;Product distribution / selectivity;

Steps:

17; 18 Preparation of Retapamulin
Example 17 Preparation of Retapamulin A 3 neck-flask (100 ml) was charged with tropine thiol (5-10 mmol), a solvent (5 vol) and a base (2.5 eq). The solvents and bases are listed in Table 1 below. Pleuromutilin mesylate (11 mmol) was then added to the flask in portions. The resulting combination was stirred at room temperature to 40° C. for 2-24 hours until full conversion to Retapamulin was achieved. Example 18Preparation of RetapamulinIn a 500 ml round bottom flask, tropine thiol (15 g), methyl isobutyl ketone (8 vol) and triethylamine (2.4 eq.) were charged. The mixture was stirred at 40° C. for 15 minutes. Pleuromutilin mesylate (1 eq.) was added. The mixture was stirred as a slurry at 40° C. for 12 hours. Water (7 vol) was added and the pH was adjusted to 8.5 using 4N HCl. The phases were separated. Water (7 vol) was added to the organic phase, the pH was adjusted to 8.2, and the phases separated again. The organic phase was extracted with water (7 vol) and the pH was adjusted to 1.5. After separation, the pH of the aqueous phase was adjusted to 12.5 with 4N NaOH. The mixture was stirred at room temperature for 20 hours. The product was vacuum filtered and washed with water. The collected crystals were dried in a 55° C. vacuum oven to yield 80% Retapamulin at 99.8% purity as determined by HPLC.

References:

Hedvati, Lilach;Gilboa, Eyal;Avhar-Maydan, Sharon;Shachan-Tov, Sharona US2009/149655, 2009, A1 Location in patent:Page/Page column 3; 5; 6

FullText

35130-97-3
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224452-66-8
210 suppliers
$5.00/5mg

References

120-29-6 Synthesis

120-29-6
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224452-66-8
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References

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