Intermediate N-protection-(2S,4S)-2-[(3-hydroxyl carbonyl)-phenyl amino formyl)]-pyrrolidine-4-thio alcohol of ertabeinan

A technology of phenylcarbamoyl and hydroxycarbonyl, applied in the field of intermediates, can solve problems such as the same or similar literature reports that have not yet been found, and achieve the effects of easy industrial production, simplified operation, and shortened reaction steps.

Inactive Publication Date: 2006-03-29
SHANGHAI JIAO TONG UNIV
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Problems solved by technology

[0004] Found through literature search to prior art, have not found the s...

Method used

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  • Intermediate N-protection-(2S,4S)-2-[(3-hydroxyl carbonyl)-phenyl amino formyl)]-pyrrolidine-4-thio alcohol of ertabeinan
  • Intermediate N-protection-(2S,4S)-2-[(3-hydroxyl carbonyl)-phenyl amino formyl)]-pyrrolidine-4-thio alcohol of ertabeinan
  • Intermediate N-protection-(2S,4S)-2-[(3-hydroxyl carbonyl)-phenyl amino formyl)]-pyrrolidine-4-thio alcohol of ertabeinan

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Embodiment Construction

[0014] Taking P as PNZ as an example, its implementation is as follows:

[0015] (1) Preparation of N-p-nitrobenzyloxycarbonyl-trans-4-hydroxyl L-pyrrolidine

[0016] Trans-4-hydroxy-L-proline (20g, 153mmol) was dissolved in water (100ml), potassium carbonate (27.5g, 1.3equ.) was added under stirring, and PNZ-Cl (37.4g , 1.1equ.) in toluene solution (35mL), insulated and stirred for 1h, and TLC monitored the reaction end point. Separate the water layer, decolorize it with activated carbon, add concentrated hydrochloric acid dropwise in an ice bath until the pH of the system is 2, and keep stirring to avoid agglomeration. After about 1 hour, let it stand for 2 hours, filter it with suction, wash it with an appropriate amount of water, and dry it until constant Weight, to obtain product 45.8g, y=96.4%.

[0017] 1H NMR (400MHz, DMSO-d6) δ: 8.23-8.16 (m, 2H, Ar-H), 7.62-7.56 (m, 2H, Ar-H), 5.26-5.11 (m, 2H, -OCH2-Ar) , 4.33-4.17(m, 2H, H-2 and H-4), 3.52-3.34(m, 2H, H-5), 2.48(...

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Abstract

An N-protective group-(2S,4S)-2-[(3-hydroxycarbonyl)-phenylaminoformyl]- pyrrolidine-4-yl thiol as the intermediate of Ertapeinan is prepared through reaction between trans-4-hydroxy-L-phrrolidine and p-nitrobenzylcarbonyl chloride to obtain N-p-nitrobenzyloxy carbonyl-trans-4-hydroxy-4-hydroxy-L-pyrrolidine, reaction by one-pot method to obtain thiolactone, and reaction on meta-aminobenzoic acid.

Description

technical field [0001] The present invention relates to an intermediate in the technical field of medicine, in particular to an intermediate N-protected-(2S,4S)-2-[(3-hydroxycarbonyl)-phenyl for the preparation of ertapenem Carbamoyl]-pyrrolidin-4-ylthiol. technical background [0002] Ertapenem (ertapenem, MK-0826, L-749,345, trade name INVANZTM) is a new type of broad-spectrum carbapenem antibiotic newly developed by Merck Pharmaceutical Company of the United States. This product was launched in the United States and Europe in November 2001 and April 2002 respectively. It is the only I-β-methyl carbapenem antibiotic for parenteral administration and has a wide range of antibacterial activities, including Gram-positive With negative aerobes and anaerobes. [0003] The raw material used in the preparation of ertapenem in the prior art is the intermediate [4R, 5S, 6S, 8R)-3-[(diphenylphosphonyloxy)oxy]- 6-(1-Hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0 hept-2-ene-2-carb...

Claims

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Application Information

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IPC IPC(8): C07D207/12
CPCY02P20/55
Inventor 张万斌刘德龙罗丽谢芳
Owner SHANGHAI JIAO TONG UNIV
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