L-Proline → HCID 54203320, compound

HRID 66532Notes

Reaction equation

HRID 66532 reaction equation
[O:1]=[C:2]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=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]>>[NH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[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])=[CH:9]1

Participants

3

Reactant 2

HCID 145742L-ProlineHCID 730037Indole-3-(4'-oxo)butyric acid

Product 1

HCID 54203320HCID 54203320, compound

Procedure

As for Example 1, 4-oxo-4-(3-indolyl)butyric acid (0.1 mole) is coupled to L-proline to give 1-[3-(3-indolylcarbonyl)propionyl]-L-proline. The preceding compound is reacted with bromine in acetic acid and the brominated derivative is reacted with sodium thioacetate in acetonitrile to give the product of the Example as a glass.

Sources & evidence

ORD record
ord-9c7f04a7ab314c66a91c079c67c92e01
Source dataset
uspto-grants-1982_08
Patent number
US04342691

Reaction notes

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