ChemicalBook CAS DataBase List Temsirolimus

Temsirolimus synthesis

2synthesis methods

Product Name:Temsirolimus
CAS Number:162635-04-3
Molecular formula:C56H87NO16
Molecular Weight:1030.29

Temsirolimus is an ester analog of rapamycin. Temsirolimus binds to and inhibits the mammalian target of rapamycin (mTOR), resulting in decreased expression of mRNAs necessary for cell cycle progression and arresting cells in the G1 phase of the cell cycle. mTOR is a serine/threonine kinase which plays a role in the PI3K/AKT pathway that is upregulated in some tumors. Temsirolimus (CCI-779) is an intravenous drug for the treatment of renal cell carcinoma (RCC), developed by Wyeth Pharmaceuticals and approved by the U.S. Food and Drug Administration (FDA) in late May 2007, and was also approved by the European Medicines Agency (EMEA) on November 2007.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

Gu, Jianxin; Ruppen, Mark E.; Raveendranath, Panolil; Chew, Warren; Shaw, Chia-Cheng. Production of rapamycin 42-ester with 2,2-bis(hydroxymethyl)propionic acid (CCI-779) and its proline analog. Assignee Wyeth, USA. US 20050234086. (2005).

162635-03-2
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162635-04-3
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Yield:162635-04-3 83.2%

Reaction Conditions:

with sulfuric acid;water in tetrahydrofuran at 0 - 5;

Steps:

2
In a 5L glass reaction bottle,Add coupling intermediate 48g, 1000ml tetrahydrofuran,Stirring temperature control is 0~5 °C,Slowly add 126ml of 2mol/L sulfuric acid solution.After the drop, the temperature is stirred at 0 to 5 ° C,TLC detects the progress of the reaction and the reaction is completed.After that, 500 ml of drinking water was added to the reaction solution.1000ml of ethyl acetate, stirring, liquid separation,Ethyl acetate500ml/time extraction twice,Combine the organic layers with 1000 ml of saturated sodium bicarbonate solution,1000ml saturated saline solutionWashing, drying anhydrous sodium sulfate 300g for 3 to 4 hours; filtering, evaporating ethyl acetate to dryness under reduced pressure to give a pale yellow foamy solid;The yield was 83.2%.

References:

Lunan Pharmaceutical Group Co., Ltd.;Zhang Guimin;Bai Wenqin;Song Chuanling;Sun Xiuling CN108948046, 2018, A Location in patent:Paragraph 0062; 0063; 0068

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162635-04-3
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References

Temsirolimus Related Search:

3-(4-Hydroxyphenyl)propionic acid Rapamycin 2,2-Bis(hydroxymethyl)propionic acid Ethyl 1-methylpipecolinate