HCID 23700354, compound → 1-[3-Acetylthio-3-(5-chloro-2-thenoyl)-2-methylpropionyl]-L-proline

HRID 66482Notes

Reaction equation

HRID 66482 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([CH2:9][CH:10]([CH3:21])[C:11]([N:13]2[CH2:20][CH2:19][CH2:18][C@H:14]2[C:15]([OH:17])=[O:16])=[O:12])=[O:8])=[CH:4][CH:3]=1.[C:22]([O-:25])(=[S:24])[CH3:23].[Na+]>C(#N)C>[C:22]([S:24][CH:9]([C:7](=[O:8])[C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH:10]([CH3:21])[C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12])(=[O:25])[CH3:23]

Participants

4

Reactant 2

HCID 23700354HCID 23700354, compoundHCID 53880190HCID 53880190, compound

Product 1

HCID 542612251-[3-Acetylthio-3-(5-chloro-2-thenoyl)-2-methylpropionyl]-L-proline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Bromination of the [S]-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 the [R-(R*,S*)] and [R-(R*,R*)] isomers of the product of the Example as a glass.

Workup

  1. customgives

Sources & evidence

ORD record
ord-de4ce3fad7264a008d4de8ea7ef562bc
Source dataset
uspto-grants-1982_08
Patent number
US04342689

Reaction notes

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