Ethyl isocyanatoacetate → HCID 15027401, compound

HRID 1461450Notes

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.[N:25]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:26]=[O:27]>>[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:26]([NH:25][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:27])=[C:9]2[CH3:22])=[O:7])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 76283Ethyl isocyanatoacetate

HCID 150273901-(4-Chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine

Product 1

HCID 15027401HCID 15027401, compoundYield 27%

Procedure

According to the procedure of Example 71, (1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-lH-indole-3-methanamine is reacted with ethyl isocyanato-acetate. The crude product is purified by column chromatography (silica gel, 1:4 ethyl acetate:methylene chloride) to give pure N-[[[[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-lH-indol-3-yl]methyl]hydroxyamino]carbonyl]glycine, ethyl ester (27%) as an amorphous solid.

Workup

customThe crude product is purified by column chromatography (silica gel, 1:4 ethyl acetate:methylene chloride)

Sources & evidence

ORD record: ord-05249d9810e14b9b842d08140aa7ecc4
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05075330

Reaction notes

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