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Synfacts 2021; 17(07): 0833
DOI: 10.1055/s-0040-1706223
Peptide Chemistry

Synthesis of N-Unprotected α-Amino Acid Methyl Esters

Contributor(s):
Hisashi Yamamoto
,
Isai Ramakrishna
Chen B.-C, *, Skoumbourdis AP, Guo P, Bednarz MS, Kocy OR, Sundeen JE, Vite GD. Bristol-Myers Squibb Pharmaceutical Research Institute, Princeton, USA
A Facile Method for the Transformation of N-(tert-Butoxycarbonyl) α-Amino Acids to N-Unprotected α-Amino Methyl Esters.

J. Org. Chem. 1999;
64: 9294-9296
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Key words

amino acid methyl esters - esterification - amino acids

Significance

N-Unprotected α-amino acid methyl­ esters play a crucial role in synthetic organic chemistry, particularly in peptide drug discovery. In 1999, Chen and co-workers developed a simple and straightforward one-pot method for the synthesis of N-unprotected α-amino acid methyl esters from N-(Boc)-protected α-amino acids.


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Comment

The transformation of N-Boc pro­tected α-amino acids into N-unprotected α-amino acid methyl esters mediated by TMSCl and MeOH proceeded smoothly and delivered the desired products in high yields and with excellent enantio­selectivities. This method does not require column chromatography for the purification of the products.


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Publication History

Article published online:
17 June 2021

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