Methyl iodide → HCID 53706700, compound

HRID 583421Notes

Reaction equation

HRID 583421 reaction equation
[CH3:1][O:2][C:3]([CH:5]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:9]=1)=[O:4].[CH3:32]I>CN(C)C=O.C(OCC)(=O)C.[Ag]>[CH3:1][O:2][C:3]([CH:5]([N:24]([CH3:32])[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:9]=1)=[O:4]

Participants

6

Reactant 2

HCID 6328Methyl iodideHCID 53876841HCID 53876841, compound

Product 1

HCID 53706700HCID 53706700, compound

Reagents, catalysts & solvents 3

HCID 23954SilverCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

295 g of silver(l) oxide are added, with stirring, to a solution of 75 g of N-tert-butyloxycarbonyl-amino-3-(1-tert-butyloxycarbonyl-indol-3-yl)-propanecarboxylic acid methyl ester in 770 ml of N,N-dimethylformamide. 75 ml of methyl iodide are then added dropwise. The reaction mixture rises to a temperature of 40° and is stirred at room temperature for 2 days and then diluted with 800 ml of ethyl acetate, filtered and concentrated by evaporation. The residue is purified by chromatography (silica gel, hexane/ethyl acetate 3:2). In this way the title compound is obtained in the form of a yellow oil.

Workup

  1. customrises to a temperature of 40°
  2. filtrationfiltered
  3. concentrationconcentrated by evaporation
  4. customThe residue is purified by chromatography (silica gel, hexane/ethyl acetate 3:2)

Sources & evidence

ORD record
ord-70e8f1dcdeae4339a510a5b7e51d7150
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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