Reaction #78296

ord-b91d4a129fa646798f6cec1ebc5927ea

Reaction equation

CC1(c2ccc(F)cc2)OC(/C=C/c2ccsc2)=CC1=O
(E)-2-(4-fluorophenyl)-2-methyl-5-[2-(3-thienyl)ethenyl]-3(2H)-furanone
O[C@H](CS)[C@H](O)CS
1,4-dithio-DL-threitol
→
CC1(c2ccc(F)cc2)OC(CC(SC[C@@H](O)[C@H](O)CS)c2ccsc2)=CC1=O
5-(2-{[(2S*,3S*)-2,3-dihydroxy-4-mercaptobutyl]thio}-2-thien-3-ylethyl)-2-(4-fluorophenyl)-2methylfuran-3(2H)-one

Reactants

CC1(c2ccc(F)cc2)OC(/C=C/c2ccsc2)=CC1=O
(E)-2-(4-fluorophenyl)-2-methyl-5-[2-(3-thienyl)ethenyl]-3(2H)-furanone
O[C@H](CS)[C@H](O)CS
1,4-dithio-DL-threitol

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Following the procedure of Method C, Example 1, (E)-2-(4-fluorophenyl)-2-methyl-5-[2-(3-thienyl)ethenyl]-3(2H)-furanone was reacted with 1,4-dithio-DL-threitol to give 5-(2-{[(2S*,3S*)-2,3-dihydroxy-4-mercaptobutyl]thio}-2-thien-3-ylethyl)-2-(4-fluorophenyl)-2methylfuran-3(2H)-one: 1H NMR (DMSO-d6) δ1.53, 1.57 and 1.60 (overlapped singlets, 3H), 4.60 (m, 1H), 5.56 and 5.57 (overlapped singlets, 1H), 7.12-7.60 (m, 7H); MS (LR-ESI) m/z 455 (M+H calcd. for C21H24FO4S3 455).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06710078B2uspto-grants-2004_03