Dichloromethane → HCID 54244115, compound

HRID 276963Notes

Reaction equation

HRID 276963 reaction equation
[N:1]12CC[CH2:9][N:8]=[C:7]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2.[CH:12]([S:15](Cl)(=[O:17])=[O:16])([CH3:14])[CH3:13].Cl[CH2:20]Cl>O>[CH3:9][N:8]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH:3]([CH3:20])[CH2:2][NH:1][S:15]([CH:12]([CH3:14])[CH3:13])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 824082-Propanesulfonyl chloride

Product 1

HCID 54244115HCID 54244115, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred suspension of the product of Preparation 5 (2.69 g, 12.5 mmol) in 50 mL of dichloromethane under N2 at 0° C. is added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (3.8 mL 27.5 mmol). The reaction mixture is stirred for 30 minutes, then isopropylsulfonyl chloride (1.7 mL, 15.0 mmol) is added dropwise. The reaction mixture is then allowed to warm to ambient temperature and stirred for 4 h. The reaction is then diluted with H2O and the layers are separated. The aqueous layer is extracted with dichloromethane and the combined organic extracts washed with saturated NaCl, dried over MgSO4 and filtered. Evaporation of the filtrate and chromatography of the residue gives the title compound.

Workup

  1. stirringstirred for 4 h
  2. customthe layers are separated
  3. extractionThe aqueous layer is extracted with dichloromethane
  4. washthe combined organic extracts washed with saturated NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customEvaporation of the filtrate and chromatography of the residue

Sources & evidence

ORD record
ord-155d231b49904966b90b2da7b52c4129
Source dataset
uspto-grants-2002_03
Patent number
US06355655B1

Reaction notes

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