Methyl iodide → HCID 54081528, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[N:4]=1.[CH3:26]N(C)CCN(C)C.C([Li])(C)(C)C.CI.[Cl-].[NH4+]>O1CCCC1.CCCCC>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])[CH3:26])[N:6]=1Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -70 °C
Procedure
The product of stage (a) above (1 g) was dissolved in dry tetrahydrofuran (20 ml) and tetramethyl ethylenediamine (1.1 ml) was added under nitrogen. The solution was cooled to -70° C. and 1.7M t-butyllithium in pentane (4.3 ml) was added dropwise. The mixture was then stirred at about -20° C. for 1 hour. It was then cooled to -70° C., and methyl iodide (0.45 g) was added. The reaction mixture was allowed to warm to 0° C. and saturated ammonium chloride solution (25 ml) was added. The mixture was extracted with tetrahydrofuran (3×50 ml) and the combined extracts were dried and evaporated to give a pale brown solid which was triturated with hexane to give 0.73 g of the desired product, mp 119°-121° C.
Workup
- temperatureIt was then cooled to -70° C.
- temperatureto warm to 0° C.
- extractionThe mixture was extracted with tetrahydrofuran (3×50 ml)
- customthe combined extracts were dried
- customevaporated
- customto give a pale brown solid which
- customwas triturated with hexane
Sources & evidence
- ORD record
- ord-8314191af66246a3afb38c50e15addcc
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05559081
Reaction notes
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