Methyl iodide → HCID 54317668, compound
Reaction equation
[Li][CH:2](CC)C.C1CCCCC1.C(=O)=O.CC(C)=O.CN(CCN(C)C)C.[CH3:27][C:28]([N:31]([CH3:43])[C:32]1[CH:42]=[CH:41][CH:40]=[CH:39][C:33]=1[C:34]([NH:36][CH2:37][CH3:38])=[O:35])([CH3:30])[CH3:29].CI>C1COCC1.O>[CH2:37]([NH:36][C:34](=[O:35])[C:33]1[C:39]([CH3:2])=[CH:40][CH:41]=[CH:42][C:32]=1[N:31]([C:28]([CH3:29])([CH3:30])[CH3:27])[CH3:43])[CH3:38]Participants
9
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
A solution of 1.3M s-BuLi in cyclohexane (9.8 mL, 12.8 mmol) was added dropwise to a dry-ice/acetone cooled solution of TMEDA (0.6 mL, 3.8 mmol) in THF (10 mL), followed by the dropwise addition of a solution of the compound of Example 188 (0.75 g, 3.2 mmol) in THF (5 mL). The reaction mixture was stirred at -78° C. for 30 min, then methyl iodide (2.3 g, 16 mmol) was introduced in a single portion. This mixture was stirred for 2.5 h at -78° C., then was warmed to -30° C., diluted with water, and extracted with EtOAc (2×). The combined organic extracts were dried (MgSO4), concentrated, and purified by HPLC with 1:4 EtOAc/cyclohexane to give 146 mg of the title compound as a light yellow solid, an 18% yield. m.p. 101°-103° C.
Workup
- stirringThis mixture was stirred for 2.5 h at -78° C.
- temperaturewas warmed to -30° C.
- extractionextracted with EtOAc (2×)
- dry with materialThe combined organic extracts were dried (MgSO4)
- concentrationconcentrated
- custompurified by HPLC with 1:4 EtOAc/cyclohexane
Sources & evidence
- ORD record
- ord-a5024e730a774ac08c55d00bf23403f4
- Source dataset
- uspto-grants-1997_12
- Patent number
- US05693667
Reaction notes
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