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Volumn , Issue 10, 2007, Pages 1513-1516

An operationally simple and efficient synthesis of orthogonally protected L-threo-β-hydroxyasparagine

Author keywords

Amides; Amino acids; Asymmetric synthesis; Peptides; Protecting groups

Indexed keywords

3 HYDROXYASPARAGINE; ASPARAGINE; ASPARTIC ACID; DICARBOXYLIC ACID DERIVATIVE; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID ANALYSIS; AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION;

EID: 34347383832 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-982544 Document Type: Article

Times cited : (16)

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21
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- L-threo-BocNH-β-OH-Asp(OMe)-OH (4, L-threo-β-Hydroxyaspartic acid (1.00 g, 5.41 mmol) was dissolved in a solution of concentrated HCl (0.89 mL, 10.8 mmol) and MeOH (18.0 mL) at 0°C. The reaction was heated at reflux for 3 h, then cooled to r.t, and concentrated in vacuo. The crude L-threo-β-OH-Asp(OMe, OH was triturated with Et2O, collected by filtration, and used without further purification in the following reaction. An aqueous solution of 10% Na2CO3 (18.0 mL) was added to L-threo- β-OH-Asp(OMe)-OH and the resulting mixture was cooled in an iced bath. A solution of Boc2O (3.65 g, 16.2 mmol) in dioxane (18.0 mL) was added dropwise to the reaction mixture and the resulting solution was stirred overnight at r.t. After concentration by rotary evaporation, the residue was dissolved in EtOAc (150 mL) and washed with 1 N HCl solution 3 x 100
- 3 solution....

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