Pmc-protected amino acid esters as substrates in N-alkylamino acid synthesis
✍ Scribed by Kazimierz Wiśniewski; Aleksandra S. Kołodziejczyk
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 186 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
N-alkylamino acids may be synthesised via Mitsunobu reaction of N-(2,2,5,7,8pentamethylchroman-6-sulphonyl-)-amino acid esters with various alcohols and subsequent deprotection.
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## Abstract Esters can be prepared from __N__‐hydroxyphthalimide and __N__‐carbobenzoxy‐ or __N__‐phthaloyl‐amino acids using dicyclohexylcarbodi‐imide as condensing agent. The compounds are suitable for the stepwise synthesis of peptides without racemization. With methanol the __N__‐hydroxyphthali
## Abstract The method works well for Boc‐ and Cbz‐protected substrates.
Chloromethylation of N-imine-protected amino acid esters followed by acid hydrolysis gave a-aminoalkyl-a%chloromethylketone as a HCl salt form in good yield without racemization. The amino group was conveniently protected with carbamate protecting reagents to give various useful intermediates for th