Hexane → HCID 22885514, compound

HRID 1289355Notes

Reaction equation

HRID 1289355 reaction equation
[C:1]1([C:7]2[S:8][CH2:9][C:10](=[O:12])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:13]([NH:23][C@H:24]([C:26](Cl)=[O:27])[CH3:25])([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14].CCCCCC>ClCCl.N1C=CC=CC=1.CC(C)=O>[C:1]1([C:7]2[S:8][CH:9]=[C:10]([O:12][C:26](=[O:27])[C@H:24]([CH3:25])[NH:23][S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 8058HexaneHCID 27487202-Phenyl-1,3-thiazol-4(5H)-oneHCID 12924680HCID 12924680, compound

Product 1

HCID 22885514HCID 22885514, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

4.43 g (0.025 mole) of 2-phenyl-4(5H)-thiazolone was dissolved in a cosolvent of 150 ml of dichloromethane and 6 ml of pyridine and cooled to 5° C. The solution of N-tosyl-L-alanyl chloride (10 g) dissolved in dichloromethane cooled to below was added to the mixture. The reacting solution was stirred, followed by standing at room temperature for 3 hours. The solution was washed with 1N citric acid, water, 5% sodium bicarbonate and a saturated sodium chloride solution in that order, dried over magnesium sulfonate, filtered; and concentrated under reduced pressure. Yellowish solid residue, so formed, was dissolved in 50 ml of acetone, and 50 ml of hexane was added to the solution. After standing the solution at room temperature for 1 hour, the thick yellowish amorphous solid, so formed, was removed. 200 ml of another hexane was added to the filtrate, followed by 10 hours' standing in the refrigerator. Filtration gave pale yellowish needle crystals as a desired compound.

Workup

  1. temperaturecooled
  2. additionto below was added to the mixture
  3. washThe solution was washed with 1N citric acid, water, 5% sodium bicarbonate
  4. dry with materiala saturated sodium chloride solution in that order, dried over magnesium sulfonate
  5. filtrationfiltered
  6. concentrationand concentrated under reduced pressure
  7. customYellowish solid residue, so formed
  8. customat room temperature
  9. customfor 1 hour
  10. customthe thick yellowish amorphous solid, so formed
  11. customwas removed
  12. addition200 ml of another hexane was added to the filtrate
  13. waitfollowed by 10 hours
  14. filtrationFiltration

Sources & evidence

ORD record
ord-204a8c76186444cab14fa2f108557027
Source dataset
uspto-grants-1998_05
Patent number
US05750359

Reaction notes

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