Bromine → 1-[3-Acetylthio-3-(5-chloro-3-thenoyl)propionyl]-L-proline

HRID 66529Notes

Reaction equation

HRID 66529 reaction equation
[Cl:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([CH2:9][CH2:10][C:11]([OH:13])=O)=[O:8])[CH:3]=1.[NH:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17].C(N1C=CN=C1)(N1C=CN=C1)=O.BrBr.[C:36]([O-:39])(=[S:38])[CH3:37].[Na+]>C(O)(=O)C.C(#N)C>[C:36]([S:38][CH:9]([C:7](=[O:8])[C:4]1[CH:3]=[C:2]([Cl:1])[S:6][CH:5]=1)[CH2:10][C:11]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13])(=[O:39])[CH3:37]

Participants

8

Reactant 5

HCID 24408BromineHCID 682631,1'-CarbonyldiimidazoleHCID 145742L-ProlineHCID 20530004HCID 20530004, compoundHCID 23700354HCID 23700354, compound

Product 1

HCID 540440671-[3-Acetylthio-3-(5-chloro-3-thenoyl)propionyl]-L-proline

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

As for Example 8, 3-(5-chloro-3-thenoyl)propionic acid is coupled to L-proline with 1,1'-carbonyldiimidazole. The coupled product 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.

Workup

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

Sources & evidence

ORD record
ord-ec0ad837663f45c6b7163b4000c21315
Source dataset
uspto-grants-1982_08
Patent number
US04342691

Reaction notes

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