Methyl iodide → HCID 67074337, compound

HRID 2095541Notes

Reaction equation

HRID 2095541 reaction equation
[C:1]([O:5][C:6](=[O:30])[CH2:7][CH:8]([N:11]1[C:17](=[O:18])[CH2:16][CH2:15][N:14]([C:19](=[O:29])/[CH:20]=[CH:21]/[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[CH2:13][CH2:12]1)[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].I[CH3:32].[H-].[Na+].OS([O-])(=O)=O.[K+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:30])[CH2:7][CH:8]([N:11]1[C:17](=[O:18])[CH2:16][CH2:15][N:14]([C:19](=[O:29])/[CH:20]=[CH:21]/[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[CH2:13][CH2:12]1)[CH2:9][O:10][CH3:32])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 67074127HCID 67074127, compound

Product 1

HCID 67074337HCID 67074337, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.200 g (0.46 mmol) of 3-{4-[(E)-3-(3-chloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-4-hydroxy-butyric acid tert-butyl ester in 0.73 ml of DMF was added dropwise 0.142 ml (2.29 mmol) of iodomethane. The solution was treated at 0° C. with 0.024 g (0.55 mmol) of NaH (55% in oil). The reaction was stirred for 3 h at 0° C., neutralized with cold aqueous 10% KHSO4 and extracted with EtOAc (3×). The organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% NaCl, dried (Na2SO4), evaporated and purified on a SiO2-column (dichloromethane/Isopropanol 99:1-98:2) to give the titled compound in 61% yield as colorless gum. MS: 451.2 (MH+, 1Cl).

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% NaCl
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. custompurified on a SiO2-column (dichloromethane/Isopropanol 99:1-98:2)

Sources & evidence

ORD record
ord-febb7ff9e8874206a6e4e50d84d12535
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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