Methyl 2,2-dimethyl-4-oxo-5-(5-chlorobenzothiazol-2-ylthio)pentanoate → 1-(p-Chlorobenzyl)-alpha,alpha-dimethyl-5-isopropyl3-(5-chlorobenzothiazol-2-ylthio)indole-2-propanoic acid

HRID 483421Notes

Reaction equation

HRID 483421 reaction equation
Cl.[Cl:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:12][CH:11]=2)N)=[CH:5][CH:4]=1.[CH3:21][C:22]([CH3:42])([CH2:27][C:28](=O)[CH2:29][S:30][C:31]1[S:32][C:33]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:34]=2[N:35]=1)[C:23]([O:25]C)=[O:24]>>[Cl:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:10]3[C:15](=[CH:14][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:12][CH:11]=3)[C:29]([S:30][C:31]3[S:32][C:33]4[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:34]=4[N:35]=3)=[C:28]2[CH2:27][C:22]([CH3:42])([CH3:21])[C:23]([OH:25])=[O:24])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 15035415Methyl 2,2-dimethyl-4-oxo-5-(5-chlorobenzothiazol-2-ylthio)pentanoateHCID 197523941-(4-Chlorobenzyl)-1-[4-(isopropyl)phenyl]hydrazine, Hydrochloride

Product 1

HCID 112732551-(p-Chlorobenzyl)-alpha,alpha-dimethyl-5-isopropyl3-(5-chlorobenzothiazol-2-ylthio)indole-2-propanoic acid

Procedure

Following the procedure of Example 104, but 1-(p-chlorobenzyl)-1-[4-(i-propyl)phenyl]-hydrazine hydrochloride and methyl 2,2-dimethyl-4-oxo-5-(5-chlorobenzothiazol-2-ylthio)pentanoate as starting materials followed by hydrolysis at reflux gave the title compound, m.p 154°-156°.

Workup

  1. customfollowed by hydrolysis
  2. temperatureat reflux

Sources & evidence

ORD record
ord-bf643c16d8ae4de4a43c87ce30c8dff0
Source dataset
uspto-grants-1993_07
Patent number
US05225421

Reaction notes

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