Methyl iodide → HCID 69223073, compound

HRID 130378Notes

Reaction equation

HRID 130378 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]2[CH:13]([CH2:33][OH:34])[CH:14]([NH:16][C:17](=[O:32])[CH2:18][NH:19][C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[CH2:15][CH:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I[CH3:36]>[Ag]=O.CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]2[CH:13]([CH2:33][O:34][CH3:36])[CH:14]([NH:16][C:17](=[O:32])[CH2:18][NH:19][C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[CH2:15][CH:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 69221122HCID 69221122, compound

Product 1

HCID 69223073HCID 69223073, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-hydroxymethyl-5-[2-(3-trifluoromethylbenzoylamino)acetylamino]octahydrocyclopenta[c]-pyrrole-2-carboxylic acid tert-butyl ester in a small amount of DMF and a large excess of iodomethane is treated with silver oxide and stirred at room temperature until the reaction is complete. The reaction mixture is filtered through Celite and concentrated under vacuum yielding a residue. The residue is purified by flash column chromatography providing the title product.

Workup

  1. filtrationThe reaction mixture is filtered through Celite
  2. concentrationconcentrated under vacuum
  3. customyielding a residue
  4. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-298976d0feae4d97bc1700f5ab74585c
Source dataset
uspto-grants-2008_06
Patent number
US07381738B2

Reaction notes

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