An improved large scale procedure for the preparation of N-Cbz amino acids

Ashok D. Pehere; Andrew D. Abell

doi:10.1016/j.tetlet.2011.01.102

An improved large scale procedure for the preparation of N-Cbz amino acids

Ashok D. Pehere, Andrew D. Abell

Chemistry (Twin Cities)

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

18 Scopus citations

Abstract

A simple and scalable method for the preparation of N-Cbz protected amino acids is presented which uses a mixture of aqueous sodium carbonate and sodium bicarbonate to maintain the appropriate pH during the addition of benzyl chloroformate. The method has been extended to other N-protections and is amenable to large scale preparation of an intermediate toward Zofenopril, an ACE inhibitor.

Original language	English (US)
Pages (from-to)	1493-1494
Number of pages	2
Journal	Tetrahedron Letters
Volume	52
Issue number	13
DOIs	https://doi.org/10.1016/j.tetlet.2011.01.102
State	Published - Mar 30 2011

Bibliographical note

Funding Information:
We thank Dr. Vinayak Gore (Mylan India Private Limited) for carrying out the large scale reactions. The authors acknowledge the financial support of an ARC DP grant (A.D.A.) and the University of Adelaide for an AFSI scholarship to A.D.P.

Keywords

Large scale
N-Cbz amino acids
Synthesis
Zofenopril

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10.1016/j.tetlet.2011.01.102

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note = "Funding Information: We thank Dr. Vinayak Gore (Mylan India Private Limited) for carrying out the large scale reactions. The authors acknowledge the financial support of an ARC DP grant (A.D.A.) and the University of Adelaide for an AFSI scholarship to A.D.P. ",

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AU - Pehere, Ashok D.

AU - Abell, Andrew D.

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PY - 2011/3/30

Y1 - 2011/3/30

N2 - A simple and scalable method for the preparation of N-Cbz protected amino acids is presented which uses a mixture of aqueous sodium carbonate and sodium bicarbonate to maintain the appropriate pH during the addition of benzyl chloroformate. The method has been extended to other N-protections and is amenable to large scale preparation of an intermediate toward Zofenopril, an ACE inhibitor.

AB - A simple and scalable method for the preparation of N-Cbz protected amino acids is presented which uses a mixture of aqueous sodium carbonate and sodium bicarbonate to maintain the appropriate pH during the addition of benzyl chloroformate. The method has been extended to other N-protections and is amenable to large scale preparation of an intermediate toward Zofenopril, an ACE inhibitor.

KW - Large scale

KW - N-Cbz amino acids

KW - Synthesis

KW - Zofenopril

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

An improved large scale procedure for the preparation of N-Cbz amino acids

Abstract

Bibliographical note

Keywords

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