2-Chlorothiophene → 4-(5-Chlorothiophen-2-yl)-4-oxobutanoic acid

HRID 66478

Reaction equation

HRID 66478 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[C:7]1(=[O:13])[O:12][C:10](=[O:11])[CH2:9][CH2:8]1>>[Cl:1][C:2]1[S:3][C:4]([C:7](=[O:13])[CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 72992-ChlorothiopheneHCID 7922Succinic anhydride

Product 1

HCID 23843244-(5-Chlorothiophen-2-yl)-4-oxobutanoic acidYield 74%

Procedure

As described for Example 1, 0.3 mole of 2-chlorothiophene is reacted with succinic anhydride to give 4-(5-chloro-2-thienyl)-4-ketobutyric acid (74%), m.p. 121°-123° C. The preceding compound is coupled to L-proline to give 1-[3-(5-chloro-2-thenoyl)propionyl]-L-proline (94%) as crystals, m.p. 131°-133° C. The above compound is reacted with bromine in acetic acid to give 1-[3-bromo-3-(5-chloro-2-thenoyl)propionyl]-L-proline as a glass. As for Example 1, reaction of the preceding compound with sodium thioacetate in ethanol gives the desired product (84%) as a glass.

Sources & evidence

ORD record
ord-16ef1e955e6e4bfeb9bd63ab25fd48b2
Source dataset
uspto-grants-1982_08
Patent number
US04342689

Linked notes

Loading…