ethyl N-carbonylcarbamate → HCID 15027400, compound

HRID 1461449Notes

Reaction equation

HRID 1461449 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.[CH2:25]([O:27][C:28]([N:30]=[C:31]=[O:32])=[O:29])[CH3:26]>O1CCCC1>[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]([NH:30][C:28](=[O:29])[O:27][CH2:25][CH3:26])=[O:32])=[C:9]2[CH3:22])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 300166ethyl N-carbonylcarbamateHCID 150273901-(4-Chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine

Product 1

HCID 15027400HCID 15027400, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-lH-indole-3-methanamine (540 mg, 1.57 mmol) in 30 ml of freshly distilled tetrahydrofuran at 0° C. is added dropwise 194 μl (1.88 mmol) of ethoxycarbonyl isocyanate. The reaction mixture is stirred for 10 minutes at 0° C. and concentrated in vacuo. The residue is purified by column chromatography on silica using an ethyl acetate:methylene chloride gradient (15:85 to 1:1). Recrystallization from methylene chloride:hexane gives pure [[[[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-lH-indol-3-yl]methyl]hydroxyamino]carbonyl]carbamic acid, ethyl ester (68%); mp 147.5°-148° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is purified by column chromatography on silica using an ethyl acetate
  3. customRecrystallization from methylene chloride

Sources & evidence

ORD record
ord-ab501415dd28499db6d548983c434739
Source dataset
uspto-grants-1991_12
Patent number
US05075330

Reaction notes

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