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Chemical Structure| 192800-77-4 Chemical Structure| 192800-77-4

Structure of 192800-77-4

Chemical Structure| 192800-77-4

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Product Details of [ 192800-77-4 ]

CAS No. :192800-77-4
Formula : C9H15ClN2O2
M.W : 218.68
SMILES Code : O=C(Cl)[C@H](C(C)C)N1CCCNC1=O

Safety of [ 192800-77-4 ]

Application In Synthesis of [ 192800-77-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 192800-77-4 ]

[ 192800-77-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 192800-77-4 ]
  • [ 192725-17-0 ]
YieldReaction ConditionsOperation in experiment
To a stirred solution of (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3- hydroxy-5-(t-butyloxycarbonylamino)-l,6-diphenylhexane (5.1 g) in methylene chloride (50 rnL) was added trifluoroacetic acid (10.65 g) at room temperature over a period of 20 minutes. The reaction mixture was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure and then water (100 mL) was added followed by methylene chloride (100 mL). To the cooled at about 10-15C biphasic mixture, solid sodium bicarbonate (12 g) was added portionwise, and finally its pH was adjusted to about 8.5 with aqueous sodium hydroxide. The organic layer was separated and washed with water (50 mL). Concentration of methylene chloride layer provided a residue as thick oil. Ethyl acetate (50 mL) was added into the above residue and stirred to yield a clear solution. To the stirred solution imidazole (2.1 g) was added at room temperature. The mixture was cooled to 00C. To the cold reaction mixture a suspension of acid chloride in dimethyl formamide (from step 1 of Example 5) was slowly added at about 0 to 50C during 30 minutes. The reaction mixture was stirred at 0 to 50C for next 30 minutes, then warmed to room temperature and stirred at room temperature for 12 hours. The reaction mixture was cooled down to 10C and quenched with aqueous hydrochloric acid (100 mL) at 10-150C. Ethyl acetate (50 mL) was added to the mixture and stirred at room temperature for 30 minutes. The organic layer was separated and washed with aqueous sodium bicarbonate (50 mL) followed by water (2 X 50 mL). Evaporation of the solvent under reduced pressure afforded crude material as an off-white solid which was dissolved in ethyl acetate (28 mL) at 45-5O0C and then heptane (28 mL) was slowly added at 50- 450C. The resulting clear solution was slowly allowed to cooled to room temperature and stirred at room temperature for 12 hours. A white solid, precipitated out from the solution was filtered and washed with 1:1 mixture of ethyl acetate and heptane (5 mL). The solid was dried under vacuum at 50-60C for 12 hours to yield the title compound as a white solid.Yield: 3.5 g
  • 2
  • [ 192800-77-4 ]
  • [ 192725-49-8 ]
  • [ 192725-17-0 ]
YieldReaction ConditionsOperation in experiment
With 1H-imidazole; dmap; In ethyl acetate; N,N-dimethyl-formamide; at 0 - 10℃; for 14h; Example 1 Thionyl chloride (18 ml) was added to the mixture of 2S-(1-tetrahydropyrimid-2-onyl)-3-methylbutanoic acid (25 gm), tetrahydrofuran (370 ml) and dimethylformamide (2 ml) at 0-10 deg C. and the mass was stirred for 1 hour 15 minutes. The mass was subjected to distillation under reduced pressure to remove excess thionyl chloride, n-heptane (45 ml) was added to the residue obtained and the solvent was distilled off. The reaction mass was slurried in dimethylformamide (105 ml). (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane (41 gm), imidazole (25 gm) and 4-(dimethylamino)pyridine (1.5 gm) were dissolved in ethyl acetate (420 ml). To the solution was added above slurried product at 0-10 deg C. The reaction mass was maintained for 14 hours and then ethyl acetate (165 ml) and water (250 ml) were added. The layers were separated, water (250 ml) was added to the organic layer and the pH was adjusted to 2.0-3.0 with dilute hydrochloric acid (6N HCl). The layers were separated, the organic layer was washed with aqueous sodium bicarbonate and then with water. The ethyl acetate was distilled off from the mass. The reaction mass was dissolved in ethyl acetate (80 ml) and n-heptane (80 ml) was added to the solution. The separated solid was stirred with ethyl acetate (290 ml) for 8 hours, filtered and dried the solid to obtain 33 gm of lopinavir ethyl acetate solvate.
 

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