Chloroform → HCID 58499943, compound

HRID 910785Notes

Reaction equation

HRID 910785 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C@@H:8]([C:10]1[N:14]([CH2:15][CH3:16])[C:13](SC)=[N:12][N:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[O-:20][S:21]([O-:24])(=S)=O.[Na+].[Na+].[OH-].[Na+].[CH:29](Cl)(Cl)Cl>>[C:1]([O:5][C:6](=[O:19])[NH:7][C@@H:8]([C:10]1[N:14]([CH2:15][CH3:16])[C:13]([S:21]([CH3:29])(=[O:24])=[O:20])=[N:12][N:11]=1)[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 4

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 58499665HCID 58499665, compound

Product 1

HCID 58499943HCID 58499943, compound

Procedure

To a chloroform (293 ml) solution of the [(R)-1-(4-ethyl-5-methylsulfanyl-4H-[1,2,4]triazol-3-yl)ethyl]-carbamic acid t-butyl ester (21.0 g) obtained in Example 8-(4), m-perchlorobenzoic acid (43.0 g) was added in four portions while being cooled with ice. The mixture was stirred for 3 hours at room temperature, and then stirred for 1 hour at 40° C. To the reaction mixture, Na2S2O3 (12.9 g) and an aqueous solution (300 ml) of sodium hydroxide (1 mol/liter) were added. The organic layer was separated, and washed with a saturated aqueous solution of sodium chloride. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel flash column chromatography using a solvent mixture of hexane and ethyl acetate. Then, the purified substance was recrystallized using hexane and chloroform to obtain [(R)-1-(4-ethyl-5-methanesulfonyl-4H-[1,2,4]triazol-3-yl)ethyl]-carbamic acid t-butyl ester as a white powder (17.2 g).

Workup

  1. temperaturewhile being cooled with ice
  2. stirringstirred for 1 hour at 40° C
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel flash column chromatography
  8. additiona solvent mixture of hexane and ethyl acetate
  9. customThen, the purified substance was recrystallized

Sources & evidence

ORD record
ord-76385c50ae4148f784e758577172bc96
Source dataset
uspto-grants-2011_09
Patent number
US08022225B2

Reaction notes

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