Solid phase synthesis of hydantoins using a carbamate linker and a novel cyclization / cleavage step

Tetrahedron Letters

Volumn 37, Issue 7, 1996, Pages 937-940

  Dressman, Bruce A ^a   Spangle, Larry A ^a   Kaldor, Stephen W ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

Carbamate; Combinatorial chemistry; Cyclization; Hydantoin; Solid phase synthesis

Indexed keywords

HYDANTOIN DERIVATIVE;

ARTICLE; DRUG BINDING; DRUG PURITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0030034999     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02395-X     Document Type: Article

References (24)

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20. 1% cross linked hydroxymethyl polystyrene (1 mmol/g) was purchased from Bachem California.
21. 13C were obtained using the procedure of Giralt (Giralt, E.; Rizo, J.; Pedroso, E. Tetrahedron 1984, 40, 4141-4152).
22. Analysis by HPLC (8X10 cm Waters Nova-Pak C18 column with a 4 μm particle size, gradient elution 0-100% acetonitrile / water containing 0.1% TFA, 1 mL/min for 30 min then 100% acetonitrile containing 0.1 % TFA, 1 mL/ min for 10 min) by area integration at 220 nm.
23. 2: C, 72.84; H, 5.75; N, 9.99. Found: C, 72.54; H, 5.68; N, 9.90. Ionspray MS (M+1, 100) 281.1.
24. Cyclic amino acid scaffolds were generally removed from the resin at lower temperature in order to reduce the amount of a methanol ring opened by-product.