1,1'-Carbonyldiimidazole → 1-[3-(benzo[b]thien-3-ylcarbonyl)propionyl]-L-proline

HRID 66479Notes

Reaction equation

HRID 66479 reaction equation
[O:1]=[C:2]([C:8]1[C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[S:11][CH:12]=1)[CH2:3][CH2:4][C:5]([OH:7])=O.[NH:17]1[CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([OH:21])=[O:20].C(N1C=CN=C1)(N1C=CN=C1)=O>>[S:11]1[CH:12]=[C:8]([C:2]([CH2:3][CH2:4][C:5]([N:17]2[CH2:24][CH2:23][CH2:22][C@H:18]2[C:19]([OH:21])=[O:20])=[O:7])=[O:1])[C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]1=2

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 145742L-ProlineHCID 127661024-(1-Benzothiophen-3-yl)-4-oxobutanoic acid

Product 1

HCID 540821291-[3-(benzo[b]thien-3-ylcarbonyl)propionyl]-L-prolineYield 78%

Procedure

The γ-oxo-benzo[b]thiophene-3-butyric acid is coupled to L-proline with 1,1'-carbonyldiimidazole to give 1-[3-(benzo[b]thien-3-ylcarbonyl)propionyl]-L-proline (78%) as a glass. As for Example 1, the preceding compound is reacted with bromine in acetic acid to give 1-[3-bromo-3-(benzo[b]thien-3-ylcarbonyl)propionyl]-L-proline as a glass (97%). Reaction with sodium thioacetate in ethanol gives the product (92%) of the Example as a glass.

Sources & evidence

ORD record
ord-362339d7c07c4aa5b19268a4f6cbc513
Source dataset
uspto-grants-1982_08
Patent number
US04342689

Reaction notes

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