Reacción #78308

ord-d790d9abdbae4f89bc5f814f6b774d13

Ecuación de reacción

CC1(c2ccccc2)OC(/C=C/c2ccsc2)=CC1=O
(E)-2-methyl-2-phenyl-5-[2-(3-thienyl)ethenyl]-3(2H)-furanone
N[C@@H](CS)C(=O)O
L-cysteine
CC1(c2ccccc2)OC(CC(SC[C@H](N)C(=O)O)c2ccsc2)=CC1=O
(2R)-2-amino-3-{[2-(5-methyl-4-oxo-5-phenyl-4,5-dihydrofuran-2yl)-1-thien-3-ylethyl]thio}propanoic acid

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

Following the procedure of Method C, Example 1, (E)-2-methyl-2-phenyl-5-[2-(3-thienyl)ethenyl]-3(2H)-furanone was reacted with L-cysteine to provide (2R)-2-amino-3-{[2-(5-methyl-4-oxo-5-phenyl-4,5-dihydrofuran-2yl)-1-thien-3-ylethyl]thio}propanoic acid: 1H NMR (DMSO-d6) δ1.50-1.60 (overlapping singlets, 3H), 2.70-3.10 (m, ˜2H), 4.00-4.25 (m, 1H), 4.64 (m, 1H), 5.50-5.57 (overlapping singlets, 1H), 7.12-7.38 (m, 6H), 7.52-7.63 (m, 2H), 8.35 (br s, ˜2H); MS (LR-ESI) m/z 402 (M-H calcd. for C20H20NO4S2 402)

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06710078B2uspto-grants-2004_03