Dichloromethane → t-butyl [(1S)-2-chloro-1-(4-iodobenzyl)ethyl]carbamate

HRID 747727Notes

Reaction equation

HRID 747727 reaction equation
C(N(CC)CC)C.CS(Cl)(=O)=O.Cl[CH2:14][Cl:15].OC[C@@H:18]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][CH:21]=1.[Cl-].[Li+]>O.CN(C)C=O>[Cl:15][CH2:14][C@@H:18]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:32])([CH3:31])[CH3:33])[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([I:26])=[CH:24][CH:25]=1

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 11372329t-butyl [(1S)-2-hydroxy-1-(4-iodobenzyl)ethyl]carbamate

Product 1

HCID 86760708t-butyl [(1S)-2-chloro-1-(4-iodobenzyl)ethyl]carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

0.27 ml (1.92 mmol) of triethylamine and 165 mg (1.44 mmol) of methanesulfonyl chloride were added to 5 ml of dichloromethane containing 360 mg (0.96 mmol) of t-butyl [(1S)-2-hydroxy-1-(4-iodobenzyl)ethyl]carbamate under cooling with ice. After stirring for 30 minutes, the temperature was elevated to room temperature, and the mixture was stirred for 15 hours. The reaction liquid was diluted with water. After the extraction with dichloromethane, the organic layer was successively washed with 1 N hydrochloric acid, 1 N sodium hydroxide and saturated aqueous NaCl solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. 10 ml of dimethylformamide and 203 mg (4.8 mmol) of lithium chloride were added to the residue, and they were stirred at 50° C. for 19 hours. The reaction liquid was diluted with water. After the extraction with ethyl acetate, the organic layer was successively washed with water and saturated aqueous NaCl solution. The solvent was evaporated, and the residue was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. temperatureunder cooling with ice
  2. customwas elevated to room temperature
  3. stirringthe mixture was stirred for 15 hours
  4. customThe reaction liquid
  5. extractionAfter the extraction with dichloromethane
  6. washthe organic layer was successively washed with 1 N hydrochloric acid, 1 N sodium hydroxide and saturated aqueous NaCl solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. stirringwere stirred at 50° C. for 19 hours
  10. customThe reaction liquid
  11. extractionAfter the extraction with ethyl acetate
  12. washthe organic layer was successively washed with water and saturated aqueous NaCl solution
  13. customThe solvent was evaporated
  14. customthe residue was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-a9ba731496a34ae88db4981174443895
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

Loading…