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Chemical Structure| 192725-50-1 Chemical Structure| 192725-50-1

Structure of 192725-50-1

Chemical Structure| 192725-50-1

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Product Details of [ 192725-50-1 ]

CAS No. :192725-50-1
Formula : C9H16N2O3
M.W : 200.23
SMILES Code : CC(C)[C@H](N1CCCNC1=O)C(O)=O
MDL No. :MFCD06797211
InChI Key :AFGBRTKUTJQHIP-ZETCQYMHSA-N
Pubchem ID :10910533

Safety of [ 192725-50-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H332
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501

Application In Synthesis of [ 192725-50-1 ]

* 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 [ 192725-50-1 ]

[ 192725-50-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 192725-49-8 ]
  • [ 192725-50-1 ]
  • [ 192725-17-0 ]
YieldReaction ConditionsOperation in experiment
90.1% 20.0 g (0.1 mol) of (2S)-(1-tetrahydropyrimidin-2-one)-3-methylbutyric acid and 100 ml of dichloromethane were added to the reaction flask.The mixture was placed under ice water, and the temperature was controlled below 10 C. 13.9 g (0.11 mol) of thionyl chloride was dropped into the reaction solution, and the addition was completed. The reaction was stirred at 0 to 10 C for 1 h.Then refluxing for 1 h to obtain (2S)-(1-tetrahydropyrimidin-2-one)-3-methylbutyryl chloride reaction solution;The reaction solution was lowered to 0-20 C, 25.3 g (0.25 mol) of triethylamine was added, and placed under ice water, and the temperature was controlled below 10 C.N-[(1S,2S,4S)-4-Amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-2-(2,6-dimethylphenoxy) Acetamide42.4g (0.095mol) was added to the reaction solution, and the addition was completed. The reaction was stirred at 0~10 C for 1 h.Then react at room temperature for 4 h,The lopinavir reaction solution was obtained; 10% sodium hydrogencarbonate 50 g was added to the lopinavir reaction solution, stirred for 1 hour, and layered.Then, the reaction liquid was washed with 25% sodium chloride 50 g and 50 g of purified water, and the layers were separated, and concentrated under reduced pressure to give an oily substance, 300 ml of ethyl acetate and 300 ml of n-heptane were added, and the mixture was heated to reflux and cooled to T=20~ At 25 C, and stir for 1 hour.Then cooled to 10 C, and stirred for 2 hours, filtered, filter cake vacuum drying at 50 C for 12 hours, 53.7 g of lopinavir finished product, yield 90.1%, HPLC purity ? 99.5%.
Example 1Thionyl chloride (18 ml) was added to the mixture of 2S-(1-tetrahydro- pyrimid-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 HCI). 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.
  • 2
  • [ 192725-50-1 ]
  • [ 192725-17-0 ]
 

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