L-Proline → HCID 53880190, compound

HRID 66504Notes

Reaction equation

HRID 66504 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([CH2:9][CH:10]([CH3:14])[C:11]([OH:13])=O)=[O:8])=[CH:4][CH:3]=1.[NH:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([OH:19])=[O:18]>>[Cl:1][C:2]1[S:6][C:5]([C:7]([CH2:9][CH:10]([CH3:14])[C:11]([N:15]2[CH2:22][CH2:21][CH2:20][C@H:16]2[C:17]([OH:19])=[O:18])=[O:13])=[O:8])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 145742L-ProlineHCID 205299953-(5-Chloro-2-thenoyl)-2-methylpropionic acid

Product 1

HCID 53880190HCID 53880190, compound

Procedure

As for Example 1, 3-(5-chloro-2-thenoyl)-2-methylpropionic acid is reacted with L-proline to give 1-[3-(5-chloro-2-thenoyl)-2-methylpropionyl]-L-proline. The mixture of diastereomers is separated. Bromination of [R]-1-[3-(5-chloro-2-thenoyl)-2-methylpropionyl]-L-proline and reaction of the brominated product with sodium thioacetate in acetonitrile gives a mixture of [S-(R*,S*)] and [S-(R*,R*)] isomers of the product of the Example as a glass.

Sources & evidence

ORD record
ord-a4eba71c228a4d88ba43acf69c956809
Source dataset
uspto-grants-1982_08
Patent number
US04342690

Reaction notes

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