L-Proline → 1-[3-(Acetylthio)-3-(benzo[b]thien-2-ylcarbonyl)-propionyl]-L-proline
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
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
- customto give the product of the Example as a glass