Sodium Acetate → 3-[[[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]methyl]hydroxyamino]-3-oxopropanoic acid, ethyl ester

HRID 703224Notes

Reaction equation

HRID 703224 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][NH:20][OH:21])=[C:9]2[CH3:22])=[O:7])=[CH:4][CH:3]=1.C([CH:27]([C:31](Cl)=[O:32])[C:28](Cl)=[O:29])C.[C:34]([O-])(=O)[CH3:35].[Na+].[O:39]1CCOCC1.O>>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][N:20]([OH:21])[C:31](=[O:32])[CH2:27][C:28]([O:29][CH2:34][CH3:35])=[O:39])=[C:9]2[CH3:22])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 517045Sodium AcetateHCID 109209242-Ethylpropanedioyl dichlorideHCID 150273901-(4-Chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamineHCID 218864351,4-Dioxane--water (1/1)

Product 1

HCID 150273923-[[[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]methyl]hydroxyamino]-3-oxopropanoic acid, ethyl esterYield 24%

Procedure

According to the procedure of Example 62, 1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine is reacted with 1.1 eq of ethyl malonyl chloride in dioxane/water (1:1) in the presence of sodium acetate (2.5 eq). The crude product is purified by column chromatography (silica gel, 3:7 acetone:hexane). The product crystallizes from the chromatography solvents upon standing to give pure 3-[[[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]methyl]hydroxyamino]-3-oxopropanoic acid, ethyl ester (24%); mp 170°-171° C. dec.

Workup

  1. customThe crude product is purified by column chromatography (silica gel, 3:7 acetone:hexane)
  2. customThe product crystallizes from the chromatography solvents

Sources & evidence

ORD record
ord-dc7cb7520a7d4aa687ff359efb5c7e8a
Source dataset
uspto-grants-1991_01
Patent number
US04981865

Reaction notes

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