Breckpot β-lactam synthesis

The Breckpot β-lactam synthesis is a name reaction in organic chemistry . The reaction was published in 1923 by Raymond Breckpot (1902-1983).

Overview reaction

In the Breckpot β-lactam synthesis, an ester of the β-amino acid reacts with a Grignard reagent to form β-lactam via a cyclization reaction .

Reaction mechanism

In the proposed reaction mechanism, an ester of the β-amino acid reacts with a Grignard reagent. A cyclization reaction follows and the β-lactam is formed.

modification

Breckpot β-lactam synthesis was extended using the Mukaiyama reagent (2-chloro-1-methylpyridinium iodide). In addition, N- methylpyidinium salt can be used.

application

Breckpot β-lactam synthesis can be used in the synthesis of β-lactam.

Individual evidence

↑ ^a ^b ^c ^d Zerong Wang: Comprehensive Organic Name Reactions and Reagents . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-63885-9 , pp. 521-523 , doi : 10.1002 / 9780470638859 ( wiley.com ).
↑ Irina Novosjolova: The Mukaiyama Reagent: An Efficient Condensation Agent . In: Synlett . tape 24 , no. 1 , 2013, p. 135 , doi : 10.1055 / s-0032-1317530 .
↑ Masaji Ohno, Susumu Kobayashi, Takamasa Iimori, Yi-Fong Wang, Toshio Izawa: Synthesis of (S) - and (R) -4 [(methoxycarbonyl) methyl] -2-azetidinone by chemicoenzymic approach . In: Journal of the American Chemical Society . tape 103 , no. 9 May 1981, pp. 2405-2406 , doi : 10.1021 / ja00399a043 .
↑ James J. Folmer, Carles Acero, Dung L. Thai, Henry Rapoport: Synthesis of Carbacephems from Serine . In: The Journal of Organic Chemistry . tape 63 , no. 23 , November 1, 1998, pp. 8170-8182 , doi : 10.1021 / jo980592s .

[:0-1] Zerong Wang: Comprehensive Organic Name Reactions and Reagents . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-63885-9 , pp. 521-523 , doi : 10.1002 / 9780470638859 ( wiley.com ).

[2] Irina Novosjolova: The Mukaiyama Reagent: An Efficient Condensation Agent . In: Synlett . tape 24 , no. 1 , 2013, p. 135 , doi : 10.1055 / s-0032-1317530 .

[3] Masaji Ohno, Susumu Kobayashi, Takamasa Iimori, Yi-Fong Wang, Toshio Izawa: Synthesis of (S) - and (R) -4 [(methoxycarbonyl) methyl] -2-azetidinone by chemicoenzymic approach . In: Journal of the American Chemical Society . tape 103 , no. 9 May 1981, pp. 2405-2406 , doi : 10.1021 / ja00399a043 .

[4] James J. Folmer, Carles Acero, Dung L. Thai, Henry Rapoport: Synthesis of Carbacephems from Serine . In: The Journal of Organic Chemistry . tape 63 , no. 23 , November 1, 1998, pp. 8170-8182 , doi : 10.1021 / jo980592s .