Acetone → HCID 68291730, compound

HRID 339901Notes

Reaction equation

HRID 339901 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][S:7]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:13][CH:12]=1)(=[O:9])=[O:8].C([Li])CCC.[CH3:34][C:35]([CH3:37])=[O:36].FC(F)(F)C(O)=O>C1COCC1.CCCCCC>[OH:36][C:35]([CH3:37])([CH3:34])[CH:10]([C:11]1[CH:12]=[CH:13][C:14]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)=[CH:15][CH:16]=1)[S:7]([NH2:6])(=[O:8])=[O:9]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6422Trifluoroacetic acidHCID 68359225HCID 68359225, compoundHCID 178418339Butyllithium

Product 1

HCID 68291730HCID 68291730, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Under inert gas, 0.264 g of N-(2,4-dimethoxybenzyl)-C-(4-morpholin-4-ylphenyl)methanesulfonamide was initially charged in 3 ml of THF and then, at −78° C., 0.85 ml of a 1.6 N butyllithium solution in hexane was added dropwise. The reaction mixture was stirred for 10 minutes and then 0.22 ml of acetone was added dropwise. The mixture was stirred at constant temperature for 30 minutes, 0.102 ml of trifluoroacetic acid was added and the mixture was allowed to come to room temperature. The solvent was removed under reduced pressure. The residue was dissolved in 4 ml of dichloromethane, and 1.2 ml of trifluoroacetic acid was added. After stirring at room temperature for 16 h, the crude product was purified in a purification laboratory by means of preparative HPLC. This gave the product with a molecular weight of 428.43 g/mol (C14H22N2O4S).

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 4 ml of dichloromethane
  5. addition1.2 ml of trifluoroacetic acid was added
  6. stirringAfter stirring at room temperature for 16 h
  7. customthe crude product was purified in a purification laboratory by means of preparative HPLC
  8. customThis gave the product with a molecular weight of 428.43 g/mol (C14H22N2O4S)

Sources & evidence

ORD record
ord-56b400a836b14de2a0b8caa3342c0ad6
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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