Efficient one-pot synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio-containing side chain of the new broad-spectrum carbapenem antibiotic ertapenem

Karel M.J. Brands; Ronald B. Jobson; Karen M. Conrad; J. Michael Williams; Brenda Pipik; Mark Cameron; Antony J. Davies; Peter G. Houghton; Michael S. Ashwood; Ian F. Cottrell; Robert A. Reamer; Derek J. Kennedy; Ulf H. Dolling; Paul J. Reider

doi:10.1021/jo011170c

Efficient one-pot synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio-containing side chain of the new broad-spectrum carbapenem antibiotic ertapenem

Karel M.J. Brands, Ronald B. Jobson, Karen M. Conrad, J. Michael Williams, Brenda Pipik, Mark Cameron, Antony J. Davies, Peter G. Houghton, Michael S. Ashwood, Ian F. Cottrell, Robert A. Reamer, Derek J. Kennedy, Ulf H. Dolling, Paul J. Reider

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33 Scopus citations

Abstract

An efficient synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio containing side chain of ertapenem (MK-0826) is described. Starting material N-(O,O-diisopropyl phosphoryl)-trans-4-hydroxy-L-proline is converted in a one-pot process to (2S)-cis-3-[[(4-mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid monohydrochloride in 70-75% overall yield via a series of six reactions. The development of each of these reactions and the isolation of the product is discussed in detail.

Original language	English (US)
Pages (from-to)	4771-4776
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	67
Issue number	14
DOIs	https://doi.org/10.1021/jo011170c
State	Published - Jul 12 2002
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo011170c

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Brands, K. M. J., Jobson, R. B., Conrad, K. M., Williams, J. M., Pipik, B., Cameron, M., Davies, A. J., Houghton, P. G., Ashwood, M. S., Cottrell, I. F., Reamer, R. A., Kennedy, D. J., Dolling, U. H., & Reider, P. J. (2002). Efficient one-pot synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio-containing side chain of the new broad-spectrum carbapenem antibiotic ertapenem. Journal of Organic Chemistry, 67(14), 4771-4776. https://doi.org/10.1021/jo011170c

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title = "Efficient one-pot synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio-containing side chain of the new broad-spectrum carbapenem antibiotic ertapenem",

abstract = "An efficient synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio containing side chain of ertapenem (MK-0826) is described. Starting material N-(O,O-diisopropyl phosphoryl)-trans-4-hydroxy-L-proline is converted in a one-pot process to (2S)-cis-3-[[(4-mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid monohydrochloride in 70-75% overall yield via a series of six reactions. The development of each of these reactions and the isolation of the product is discussed in detail.",

author = "Brands, {Karel M.J.} and Jobson, {Ronald B.} and Conrad, {Karen M.} and Williams, {J. Michael} and Brenda Pipik and Mark Cameron and Davies, {Antony J.} and Houghton, {Peter G.} and Ashwood, {Michael S.} and Cottrell, {Ian F.} and Reamer, {Robert A.} and Kennedy, {Derek J.} and Dolling, {Ulf H.} and Reider, {Paul J.}",

year = "2002",

month = jul,

day = "12",

doi = "10.1021/jo011170c",

language = "English (US)",

volume = "67",

pages = "4771--4776",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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}

Brands, KMJ, Jobson, RB, Conrad, KM, Williams, JM, Pipik, B, Cameron, M, Davies, AJ, Houghton, PG, Ashwood, MS, Cottrell, IF, Reamer, RA, Kennedy, DJ, Dolling, UH & Reider, PJ 2002, 'Efficient one-pot synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio-containing side chain of the new broad-spectrum carbapenem antibiotic ertapenem', Journal of Organic Chemistry, vol. 67, no. 14, pp. 4771-4776. https://doi.org/10.1021/jo011170c

TY - JOUR

T1 - Efficient one-pot synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio-containing side chain of the new broad-spectrum carbapenem antibiotic ertapenem

AU - Brands, Karel M.J.

AU - Jobson, Ronald B.

AU - Conrad, Karen M.

AU - Williams, J. Michael

AU - Pipik, Brenda

AU - Cameron, Mark

AU - Davies, Antony J.

AU - Houghton, Peter G.

AU - Ashwood, Michael S.

AU - Cottrell, Ian F.

AU - Reamer, Robert A.

AU - Kennedy, Derek J.

AU - Dolling, Ulf H.

AU - Reider, Paul J.

PY - 2002/7/12

Y1 - 2002/7/12

N2 - An efficient synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio containing side chain of ertapenem (MK-0826) is described. Starting material N-(O,O-diisopropyl phosphoryl)-trans-4-hydroxy-L-proline is converted in a one-pot process to (2S)-cis-3-[[(4-mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid monohydrochloride in 70-75% overall yield via a series of six reactions. The development of each of these reactions and the isolation of the product is discussed in detail.

AB - An efficient synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio containing side chain of ertapenem (MK-0826) is described. Starting material N-(O,O-diisopropyl phosphoryl)-trans-4-hydroxy-L-proline is converted in a one-pot process to (2S)-cis-3-[[(4-mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic acid monohydrochloride in 70-75% overall yield via a series of six reactions. The development of each of these reactions and the isolation of the product is discussed in detail.

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Efficient one-pot synthesis of the 2-aminocarbonylpyrrolidin-4-ylthio-containing side chain of the new broad-spectrum carbapenem antibiotic ertapenem

Abstract

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