Carbon Dioxide → HCID 59305017, compound

HRID 2240230Notes

Reaction equation

HRID 2240230 reaction equation
[CH2:1]([N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([F:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:29](=[O:31])=[O:30].O>C1COCC1.CCCCCC>[CH2:17]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:14]=[C:13]([F:15])[C:12]([C:29]([OH:31])=[O:30])=[C:11]([F:16])[CH:10]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 10804810HCID 10804810, compoundHCID 178418339Butyllithium

Product 1

HCID 59305017HCID 59305017, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

At −78° C., 10.0 g (32.3 mmol) of N,N-dibenzyl-3,5-difluoroaniline (Florvall, Lennart; Fagervall, Ingrid; Larsson, Lars-Gunnar; Ross, Svante B.; Eur. J. Med. Chem. Chim. Ther. 1999, 34, 137-152.) are initially charged in 90 ml of THF. 12.9 ml (32.3 mmol) of a 2.5 M solution of n-butyl-lithium in hexane are added dropwise, and the mixture is stirred at this temperature for 45 min. Excess dry ice is then added. The mixture is stirred at this temperature for another hour and then allowed to warm slowly to RT. Water is added to the reaction solution, which is then extracted twice with tert-butyl methyl ether. The aqueous phase is acidified with 10 ml of 4N hydrochloric acid, resulting in the formation of a precipitate. The mixture is extracted twice with dichloromethane, the combined phases are dried over sodium sulfate and the solvent is removed under reduced pressure.

Workup

  1. stirringThe mixture is stirred at this temperature for another hour
  2. extractionis then extracted twice with tert-butyl methyl ether
  3. customresulting in the formation of a precipitate
  4. extractionThe mixture is extracted twice with dichloromethane
  5. dry with materialthe combined phases are dried over sodium sulfate
  6. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-9de237a32a984a5c986a39e728bc2f9d
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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