L-Proline → 1-[3-(Acetylthio)-3-(benzo[b]thien-2-ylcarbonyl)-propionyl]-L-proline

HRID 66503Notes

Reaction equation

HRID 66503 reaction equation
[O:1]=[C:2]([C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[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].[C:25]([O-:28])(=[S:27])[CH3:26].[Na+]>>[C:25]([S:27][CH:3]([C:2]([C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[CH:9]=1)=[O:1])[CH2:4][C:5]([N:17]1[CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([OH:21])=[O:20])=[O:7])(=[O:28])[CH3:26]

Participants

4

Reactant 3

HCID 145742L-ProlineHCID 2986014-(1-Benzothiophen-2-yl)-4-oxobutanoic acidHCID 23700354HCID 23700354, compound

Product 1

HCID 539380211-[3-(Acetylthio)-3-(benzo[b]thien-2-ylcarbonyl)-propionyl]-L-proline

Procedure

As for Example 4, γ-oxo-benzo[b]thiophene-2-butyric acid is coupled to L-proline. The coupled product is brominated and reacted with sodium thioacetate to give the product of the Example as a glass.

Workup

  1. customto give the product of the Example as a glass

Sources & evidence

ORD record
ord-5768a81cf11d44f6b8a060ea1c51f28b
Source dataset
uspto-grants-1982_08
Patent number
US04342690

Reaction notes

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