Synthesis of 9-fluorenylmethyl esters using 9- fluorenylmethylchloroformate

Tetrahedron Letters

Volumn 40, Issue 4, 1999, Pages 753-754

  Merette S A M ^a   Burd, A P ^a   Deadman, J J ^a  

^a THROMBOSIS RESEARCH INSTITUTE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

9 FLUORENYLMETHYL ESTER DERIVATIVE; ESTER DERIVATIVE; FORMIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033593558     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02364-8     Document Type: Article

References (9)

1. Kessler, H.; Siegmeier, R. Tetrahedron Lett., 1983, 24, 281-282
2. Froussios, C.; Kolovos, M. Tetrahedron Lett., 1989, 26, 3413-3414
3. Bednarek, M.A.; Bodansky, M. Int. J. Peptide Protein Res., 1983, 21, 196-201
4. Jouin, P.; Castro, B.; Zeggaf, C.; Pantaloni, A. Tetrahedron Lett., 1987, 28, 1661-1664
5. Kim, S.; Lee, J.I.; Kim, Y.C. J. Org. Chem., 1985, 50, 560-565
6. To a solution of N-protected amino acid (about 0.02 moles) and DIPEA (1 eq.) in dry dichloromethane (80 ml) is added, at 0°C, a solution of 9-fluorenylmethylchloroformate (1.1 eq.) dissolved in DCM (20 ml). The mixture is stirred for 5 minutes before adding DMAP (0.1-0.15 eq.), then about 30 minutes at 0°C. Decarboxylation is observed throughout the reaction. Once the evolution of gas ceased, the reaction mixture is diluted with DCM and worked up using acid and base washes.
7. Albericio, F.; Nicolás, E.; Rizo, J.; Ruiz-Gayo, M.; Pedroso, E.; Giralt, E.S. Synthesis, 1990,119-122
8. Carpino, L.A. J. Org. Chem., 1988, 53, 875-885
9. Chiral chromatography was carried out at room temperature using a CHIRALCEL OD column (0.46 cm I.D. x 25 cm); Eluent: EtOH (0.1% DEA); Flow rate: 0.5-0.9 ml/min., Boc-(L)Phe-OFm: 11.5 min., Boc-(D)Phe-OFm: 16.8 min., Boc-(L)Phg-OFm: 11.7 min., Boc-(D)Phg-OFm: 12.2 min.