Methyl iodide → HCID 90064493, compound

HRID 528507Notes

Reaction equation

HRID 528507 reaction equation
[CH3:1][CH:2]1[C:10]2[CH:9]=[C:8]3[O:11][CH2:12][O:13][C:7]3=[CH:6][C:5]=2[C:4](=[O:14])[N:3]1[CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1.O1CCC[CH2:31]1.C([N-]C(C)C)(C)C.[Li+].IC>CCCCCCC.O.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:31])[C:10]2[CH:9]=[C:8]3[O:11][CH2:12][O:13][C:7]3=[CH:6][C:5]=2[C:4](=[O:14])[N:3]1[CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:19][CH2:18]1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 2724682Lithium diisopropylamideHCID 90064484HCID 90064484, compound

Product 1

HCID 90064493HCID 90064493, compoundYield 54.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Conditions

Temperature
-12.5 °C

Procedure

To a reaction vessel, 10 g (0.025 mol) compound XIII and 100 ml tetrahydrofuran were added, stirred, under nitrogen, the mixture was cooled to −10-−15° C., 48 ml (0.096 mol, 2 mol/L) solution of lithium diisopropylamide in n-heptane was added dropwise for about 30 min, after the addition was complete, the reaction was kept for 30 min, and then 1.6 ml (0.026 mol) iodomethane was added dropwise, after the addition was complete, the mixture was warmed to room temperature and then stirred for 1 h, after the reaction was complete, 300 ml ethyl acetate and 150 ml water were added, extracted and washed, the organic layer was collected, dried over sodium sulfate, filtered, the filtrate was concentrated to dry under reduced pressure, separated by column chromatography, and 5.6 g compound XIV was obtained, with yield of 54.2%. MS (ESI): m/z 417 [M+H]+.

Workup

  1. additionafter the addition
  2. additionafter the addition
  3. temperaturethe mixture was warmed to room temperature
  4. stirringstirred for 1 h
  5. extractionextracted
  6. washwashed
  7. customthe organic layer was collected
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated
  11. customto dry under reduced pressure
  12. customseparated by column chromatography

Sources & evidence

ORD record
ord-d2c3fbde780b47b2b91b0838cd198bb6
Source dataset
uspto-grants-2016_05
Patent number
US09346818B2

Reaction notes

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