Diisopropylethylamine → HCID 24876089, compound

HRID 73852Notes

Reaction equation

HRID 73852 reaction equation
C(N(CC)C(C)C)(C)C.[C:10]1([CH2:16][O:17][C:18]([NH:20][C:21]2([C:27]([NH:29][C@H:30]([CH2:34][OH:35])[CH:31]([CH3:33])[CH3:32])=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CS(C)=O.C(Cl)Cl>[C:10]1([CH2:16][O:17][C:18]([NH:20][C:21]2([C:27]([NH:29][C@H:30]([CH:34]=[O:35])[CH:31]([CH3:33])[CH3:32])=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 24875999N-[[1-[[(Phenylmethoxy)carbonyl]amino]cyclohexyl]carbonyl]-L-valinol

Product 1

HCID 24876089HCID 24876089, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Under an argon gas atmosphere, 1.22 g (9.44 mmol) of N,N-diisopropylethylamine was added dropwise to a solution of 1.50 g (9.44 mmol) of sulfur trioxide-pyridine complex in 10 ml of anhydrous dimethyl sulfoxide and 5 ml of anhydrous methylene chloride under ice-cooling, and the mixture was stirred for 15 minutes. Further, under ice-cooling, a solution of 570 mg (1.57 mmol) of N-[[1-[[(phenylmethoxy)carbonyl]amino]cyclohexyl]carbonyl]-L-valinol in 3 ml of anhydrous dimethyl sulfoxide was added to the reaction solution, and the mixture was stirred at the same temperature for 2 hours. The reaction solution was poured to ice-water and extracted with ethyl acetate twice. After the organic layer was washed with a 10% aqueous citric acid solution, a saturated aqueous sodium hydrogencarbonate solution and then saturated brine and dried with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. 20 ml of diisopropyl ether was added to the residue, and the mixture was stirred at room temperature for 18 hours. The obtained crystal was collected by filtration to obtain 435 mg (77%) of the title compound.

Workup

  1. temperaturecooling
  2. temperatureFurther, under ice-cooling
  3. stirringthe mixture was stirred at the same temperature for 2 hours
  4. extractionextracted with ethyl acetate twice
  5. washAfter the organic layer was washed with a 10% aqueous citric acid solution
  6. dry with materiala saturated aqueous sodium hydrogencarbonate solution and then saturated brine and dried with anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. addition20 ml of diisopropyl ether was added to the residue
  9. stirringthe mixture was stirred at room temperature for 18 hours
  10. filtrationThe obtained crystal was collected by filtration

Sources & evidence

ORD record
ord-8891ca4865e4470cb7e04c97ce0b145c
Source dataset
uspto-grants-2014_09
Patent number
US08829209B2

Reaction notes

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