Hexachloroethane → HCID 53907030, compound
Reaction equation
[Li]C(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].[Cl:44]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1.O>[Cl:44][C:39]1[CH:40]=[CH:41][CH:42]=[C:32]([N:31]([C:28]([CH3:29])([CH3:30])[CH3:27])[CH3:43])[C:33]=1[C:34]([NH:36][CH2:37][CH3:38])=[O:35]Participants
9
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
A solution of 1.3M s-BuLi in cyclohexane (5.7 mL, 7.5 mmol) was added dropwise to a dry-ice/acetone cooled solution of TMEDA (0.5 mL, 3.6 mmol) in THF (10 mL), followed by the dropwise addition of a solution of the compound of Example 188 (0.7 g, 3.0 mmol) in THF (5 mL). The reaction mixture was stirred at -78° C. for 30 min, then hexachloroethane (2.1 g, 9.0 mmol) in THF (5 mL) was added. This mixture was stirred for 30 min 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 3:17 EtOAc/cyclohexane to give 495 mg of the title compound as a yellow solid, an 61% yield. m.p. 106-108° C.
Workup
- stirringThis mixture was stirred for 30 min 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 3:17 EtOAc/cyclohexane
Sources & evidence
- ORD record
- ord-220d5af25112460f9ef78479795f273d
- Source dataset
- uspto-grants-1996_03
- Patent number
- US05498630
Reaction notes
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