Water → HCID 22176532, compound

HRID 1797174Notes

Reaction equation

HRID 1797174 reaction equation
[CH3:1][CH:2]([S:4](Cl)(=[O:6])=[O:5])[CH3:3].[NH2:8][CH2:9][C:10]([C:13]1[CH:18]=[CH:17][C:16]([I:19])=[CH:15][CH:14]=1)([OH:12])[CH3:11].O>C(Cl)Cl>[OH:12][C:10]([C:13]1[CH:14]=[CH:15][C:16]([I:19])=[CH:17][CH:18]=1)([CH3:11])[CH2:9][NH:8][S:4]([CH:2]([CH3:3])[CH3:1])(=[O:6])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 824082-Propanesulfonyl chlorideHCID 22176527HCID 22176527, compound

Product 1

HCID 22176532HCID 22176532, compoundYield 19.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a 250 mL 3 necked flask fitted with a stirrer and thermometer, was added dropwise 2-propanesulfonyl chloride (1.60 g, 0.011 mol) to 1-amino-2-(4-iodophenyl)propan-2-ol (2.77 gm, 0.01 mol) in 125 mL CH2Cl2 while stirring at 0° C. under nitrogen. The reaction was then allowed to warm to room temperature and stirred overnight at this temperature. In the morning, the mixture was poured into H2O and the layers were separated. The organic layer was washed once with H2O, dried over anhydrous Na2SO4, filtered, and concentrated under reduced vacuum. The resulting semi-solid was purified via silica gel chromatography employing the Prep. LC-2000 and eluting with a solvent of Hexane/EtOAc 3:1 to provide the intermediate title compound (744 mg, 19%) as a solid material. FDMS 382 (M*).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight at this temperature
  3. customthe layers were separated
  4. washThe organic layer was washed once with H2O
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced vacuum
  8. customThe resulting semi-solid was purified via silica gel chromatography
  9. washLC-2000 and eluting with a solvent of Hexane/EtOAc 3:1

Sources & evidence

ORD record
ord-5a5562e6d3bc4cf6a97053327f47bb0e
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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