Enantioselective synthesis of (L)-Fmoc-α-Me-Lys(Boc)-OH via diastereoselective alkylation of oxazinone as a chiral auxiliary

Tetrahedron Letters

Volumn 50, Issue 49, 2009, Pages 6913-6915

  Chauhan, Satendra S ^a  

^a Bachem Holding AG   (Switzerland)

Author keywords

Amino acids; Asymmetric synthesis; Chiral auxiliary; Diastereoselective alkylation; Regioselective protection

Indexed keywords

1,4 DIIODOBUTANE; BENZYL 6 OXO 2,3 DIPHENYL 4 MORPHOLINECARBOXYLATE; BUTANE; CARBOXYLIC ACID DERIVATIVE; FLUORENYLMETHYLOXYCARBONYL ALPHA METHIONYLLYSYINE TERT BUTYLHYDROXIDE; HYDROXIDE; METHYL IODIDE; OXAZINE DERIVATIVE; OXAZINONE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL STRUCTURE; HYDROGENATION; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 70350018529     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.148     Document Type: Article

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23. 18, reversed-phase column (Vydac, 150 × 4.6 mM, 5 μ). A linear gradient from 5% to 95% buffer B in 45 min was used. Buffer A consisted of 0.1% TFA in water and buffer B was 0.1% TFA in acetonitrile. Flow rate was 1.5 mL/min. Compound 16 eluted at 24.4 min under these conditions.
24. 2H: C, 60.92; H, 6.21; N, 5.01. Found: C, 60.78, H, 6.14; N, 5.08.