Diisopropylethylamine → N-[[1-[(2-Benzothienylcarbonyl)amino]cyclohexyl]carbonyl]-L-methioninal

HRID 1851850Notes

Reaction equation

HRID 1851850 reaction equation
C(N(CC)C(C)C)(C)C.[S:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:12]=[C:11]1[C:19]([NH:21][C:22]1([C:28]([NH:30][C@H:31]([CH2:36][OH:37])[CH2:32][CH2:33][S:34][CH3:35])=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:20]>CS(C)=O.C(Cl)Cl>[S:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:12]=[C:11]1[C:19]([NH:21][C:22]1([C:28]([NH:30][C@H:31]([CH:36]=[O:37])[CH2:32][CH2:33][S:34][CH3:35])=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:20]

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 57672844N-[[1-[(2-Benzothienylcarbonyl)amino]cyclohexyl]carbonyl]-L-methioninol

Product 1

HCID 57672895N-[[1-[(2-Benzothienylcarbonyl)amino]cyclohexyl]carbonyl]-L-methioninal

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

Under an argon gas atmosphere, 245 mg (1.9 mmol) of N,N-diisopropylethylamine was added dropwise to a solution of 297 mg (1.9 mmol) of sulfur trioxide-pyridine complex in 10 ml of anhydrous dimethyl sulfoxide and 5 ml of anhydrous methylene chloride under ice-cooling, the mixture was stirred for 15 minutes. Further, under ice-cooling, 100 mg (0.23 mmol) of N-[[1-[(2-benzothienylcarbonyl)amino]cyclohexyl]carbonyl]-L-methioninol was added to the reaction solution, and the mixture was stirred at the same temperature for 2 hours. The reaction solution was poured into ice-water, and the mixture was 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 quantitatively give the title compound.

Workup

  1. temperaturecooling
  2. temperatureFurther, under ice-cooling
  3. stirringthe mixture was stirred at the same temperature for 2 hours
  4. extractionthe mixture was extracted 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-7176758650f94694990b31d6a9e603c6
Source dataset
uspto-grants-2015_02
Patent number
US08957205B2

Reaction notes

Loading…