Succinic anhydride → 4-(5-Bromo-2-thienyl)-4-oxobutyric acid

HRID 66500

Reaction equation

[Br: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>>[Br: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

Reactant 2

HCID 7922Succinic anhydride

HCID 138512-Bromothiophene

Product 1

HCID 111846044-(5-Bromo-2-thienyl)-4-oxobutyric acidYield 51%

Procedure

As described for Example 1, 0.3 mole of 2-bromothiophene is reacted with succinic anhydride to give 4-(5-bromo-2-thienyl)-4-ketobutyric acid (51%), m.p. 141°-143° C. The preceding compound is coupled to L-proline to give 1-[3-(5-bromo-2-thenoyl)propionyl]-L-proline (56%) as crystals, m.p. 166°-168° C. The preceding compound (0.008 mole) is reacted with bromine in acetic acid to yield 1-[3-bromo-3-(5-bromo-2-thenoyl)propionyl]-L-proline as a glass (97%). As for Example 1, reaction of the preceding compound with sodium thioacetate gives the product of the Example (88%) as a yellow glass.

Sources & evidence

ORD record: ord-08e66090920849ff8bda41d9036f9ed0
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04342690

Linked notes

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