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

Research output: Contribution to journal › Article › peer-review

35 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

@article{4be6daf5f166420799d79fdcdedd2086,

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",

number = "14",

}

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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UR - https://www.scopus.com/pages/publications/0037067333#tab=citedBy

U2 - 10.1021/jo011170c

DO - 10.1021/jo011170c

M3 - Article

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AN - SCOPUS:0037067333

SN - 0022-3263

VL - 67

SP - 4771

EP - 4776

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 14

ER -

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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