Methyl chloroformate → HCID 24895908, compound

HRID 1187979Notes

Reaction equation

HRID 1187979 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:29]([F:32])([F:31])[F:30])[O:13][N:12]=[C:11]([C:14]3[CH:27]=[CH:26][C:17]([C:18]([NH:20][C:21]([NH:23][CH2:24][CH3:25])=[O:22])=[O:19])=[C:16]([CH3:28])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C[Si](C)(C)N[Si](C)(C)C.[Li].Cl[C:44]([O:46][CH3:47])=[O:45]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:29]([F:30])([F:32])[F:31])[O:13][N:12]=[C:11]([C:14]3[CH:27]=[CH:26][C:17]([C:18]([NH:20][C:21]([N:23]([CH2:24][CH3:25])[C:44]([O:46][CH3:47])=[O:45])=[O:22])=[O:19])=[C:16]([CH3:28])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 57426343Lithium bis(trimethylsilyl)amideHCID 67163725HCID 67163725, compound

Product 1

HCID 24895908HCID 24895908, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a solution of 0.50 g of N-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl benzoyl]-N′-ethyl urea synthesized similarly to Synthetic Example 26 in 4 mL of tetrahydrofuran, 4 mL of 1M tetrahydrofuran solution of lithium hexamethyl disilazane was added at −78° C. with stirring, and stirred at the same temperature for 30 minutes. Then, 0.12 g of methyl chloroformate was added in the reaction mixture at −78° C. with stirring. After the completion of the addition dropwise, it was continued to stir further for 18 hours while the temperature was slowly raised to room temperature. After the completion of the reaction, 30 mL of ice water was added, and extracted with ethyl acetate (30 mL×2). The organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (gradient of 0:1 to 1:2) to obtain 0.29 g of the aimed product as colorless resinous substance.

Workup

  1. stirringstirred at the same temperature for 30 minutes
  2. stirringwith stirring
  3. additionAfter the completion of the addition dropwise
  4. stirringto stir further for 18 hours while the temperature
  5. additionwas added
  6. extractionextracted with ethyl acetate (30 mL×2)
  7. dry with materialdried over saturated sodium chloride aqueous solution and anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-e17cb49d2a884d879d7bbc72b4ae62b3
Source dataset
uspto-grants-2014_03
Patent number
US08673951B2

Reaction notes

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