Acetone → HCID 68291820, compound

HRID 339913Notes

Reaction equation

HRID 339913 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][S:7]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[CH:13][CH:12]=1)(=[O:9])=[O:8].C([Li])CCC.[CH3:36][C:37]([CH3:39])=[O:38].FC(F)(F)C(O)=O>C1COCC1.CCCCCC>[OH:38][C:37]([CH3:39])([CH3:36])[CH:10]([C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)=[CH:15][CH:16]=1)[S:7]([NH2:6])(=[O:8])=[O:9]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6422Trifluoroacetic acidHCID 68291906HCID 68291906, compoundHCID 178418339Butyllithium

Product 1

HCID 68291820HCID 68291820, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of N-(2,4-dimethoxybenzyl)-C-[4-(2-morpholin-4-ylethyl)phenyl]methanesulfonamide (50 mg) in THF (1 ml) was initially charged and then, at −78° C., 1.6 N butyllithium solution in hexane (0.3 ml) was added dropwise. The reaction mixture was stirred for 10 minutes, and then acetone (50 μl) was added dropwise. The mixture was stirred at constant temperature for 30 minutes, trifluoroacetic acid (40 μl) was added and the mixture was allowed to come to room temperature. The solvent was removed under reduced pressure. The residue was dissolved in 2 ml of dichloromethane, and 250 μl of trifluoroacetic acid were added. After stirring at room temperature for 2 h, the mixture was diluted with dichloromethane and extracted with 1 M hydrochloric acid. The aqueous phase was concentrated and the residue was coevaporated with toluene. This gave the crude product with a molecular weight of 378.9 g/mol (C16H26N2O4S), which was used without further purification.

Workup

  1. stirringThe mixture was stirred at constant temperature for 30 minutes
  2. customto come to room temperature
  3. customThe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in 2 ml of dichloromethane
  5. addition250 μl of trifluoroacetic acid were added
  6. stirringAfter stirring at room temperature for 2 h
  7. additionthe mixture was diluted with dichloromethane
  8. extractionextracted with 1 M hydrochloric acid
  9. concentrationThe aqueous phase was concentrated

Sources & evidence

ORD record
ord-faa3720a325a4ded8a4f18456eb3e68c
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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