Methyl iodide → HCID 11540004, compound

HRID 2242590Notes

Reaction equation

[CH2:1]([NH:3][C:4](=[O:33])[NH:5][CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:31])([CH3:30])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:15][C:14]=2[OH:32])[CH:10]=[CH:11][CH:12]=1)[CH3:2].IC.[C:36]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:1]([NH:3][C:4](=[O:33])[NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:31])([CH3:30])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:29])[C:25]([CH3:27])([CH3:26])[CH3:28])=[CH:15][C:14]=2[O:32][CH3:36])[CH:8]=1)[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 35 (0.23 g, 0.508 mmol, 1.0 eq), iodomethane (0.13 mL, 2.1 mmol, 4.1 eq), and K2CO3 (0.56 g, 4.06 mmol, 8.0 eq) in acetone (5 mL) was heated to 70° C. for 24 hours. LC/MS showed complete conversion. Acetone was removed under reduced pressure, and the residue was partitioned in water/ethyl acetate. The aqueous layer was extracted with ethyl acetate (2×20 mL), and the combined organic layer was washed by water (20 mL), brine (20 mL) and dried over anhydrous K2CO3. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (neutral aluminum gel, 0-3% methanol in dichloromethane). Yield: 63%, 99% pure. M+1=468

Workup

customAcetone was removed under reduced pressure
customthe residue was partitioned in water/ethyl acetate
extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
washthe combined organic layer was washed by water (20 mL), brine (20 mL)
dry with materialdried over anhydrous K2CO3
customThe solvent was removed under reduced pressure
customthe residue was purified by column chromatography (neutral aluminum gel, 0-3% methanol in dichloromethane)

Sources & evidence

ORD record: ord-694453c734884f96ac5b75d1076146b3
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07671052B2

Reaction notes

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