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Chemical Structure| 66866-69-1 Chemical Structure| 66866-69-1
Chemical Structure| 66866-69-1

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CAS No.: 66866-69-1

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Synonyms: (S)-4-Methyl-2-(methylamino)pentanoic acid hydrochloride

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Product Details of N-D-Leu-OMe·HCl

CAS No. :66866-69-1
Formula : C7H16ClNO2
M.W : 181.66
SMILES Code : CC(C)C[C@H](NC)C(O)=O.[H]Cl
Synonyms :
(S)-4-Methyl-2-(methylamino)pentanoic acid hydrochloride
MDL No. :MFCD00754493
InChI Key :QYFWCUVWMMTENJ-RGMNGODLSA-N
Pubchem ID :2777992

Safety of N-D-Leu-OMe·HCl

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of N-D-Leu-OMe·HCl

* 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 [ 66866-69-1 ]

[ 66866-69-1 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 202273-47-0 ]
  • [ 66866-69-1 ]
  • 2
  • [ 61-90-5 ]
  • 2-<α-acetylamino-styryl>-4-benzyliden-Δ2-oxazolinone-(5) [ No CAS ]
  • [ 66866-69-1 ]
  • 3
  • [ 6458-39-5 ]
  • [ 66866-69-1 ]
  • 4
  • [ 202273-39-0 ]
  • [ 66866-69-1 ]
  • 5
  • [ 66866-69-1 ]
  • [ 10203-89-1 ]
YieldReaction ConditionsOperation in experiment
97% With lithium aluminium tetrahydride; In tetrahydrofuran;Reflux; To a solution of <strong>[66866-69-1](S)-4-methyl-2-(methylamino)pentanoic acid hydrochloride</strong> salt (11, 5.0 g, 27.5 mmol) in dry THF (20 mL) was added lithium aluminium hydride (LAH) (33.0 mmol, 1 M solution in THF) dropwise at 5 C. The reaction mixture was refluxed for overnight and cooled to -5 C. Unreacted LAH was quenched with aq NaOH (0.8 g, 20.0 mmol, 2 N) and the mixture was stirred at room temperature for additional 30 min. The mixture was filtered, and was washed with diethyl ether (100 mL). The filtrate was dried over MgSO4 and solvent was removed under reduced pressure to obtain the product as colorless oil (3.5 g, 26.2 mmol, 97.0%). The product was analyzed by NMR and LC-MS and used in the next step without further purification.
  • 6
  • [ 66866-69-1 ]
  • [ 1416726-19-6 ]
  • 7
  • [ 66866-69-1 ]
  • [ 1416726-29-8 ]
  • 8
  • [ 66866-69-1 ]
  • [ 1416726-21-0 ]
  • 9
  • [ 66866-69-1 ]
  • [ 1416726-20-9 ]
  • 10
  • [ 66866-69-1 ]
  • [ 1416726-25-4 ]
  • 11
  • [ 67-56-1 ]
  • [ 66866-69-1 ]
  • [ 35026-08-5 ]
  • 12
  • [ 66866-69-1 ]
  • (S)-N-[1-({(S,E)-1-[4-(aminomethyl)phenyl]-4-(methylsulfonyl)but-3-en-2-yl}amino)-4-methyl-1-oxopentan-2-yl]-2-[(S)-2-azido-3-phenylpropanamido]-N,4-dimethylpentanamide trifluoroacetic acid salt [ No CAS ]
  • 13
  • [ 66866-69-1 ]
  • (S)-2-[(S)-2-azido-3-phenylpropanamido]-N,4-dimethyl-N-(4-methyl-1-[(S,E)-5-methyl-1-(methylsulfonyl)hex-1-en-3-yl]amino}-1-oxopentan-2-yl)pentanamide [ No CAS ]
  • 14
  • [ 66866-69-1 ]
  • [ 934715-69-2 ]
  • 15
  • [ 66866-69-1 ]
  • methyl N-[(S)-2-azido-3-phenylpropanoyl]-L-leucyl}-N-methyl-L-leucinate [ No CAS ]
  • 16
  • [ 66866-69-1 ]
  • (S)-2-[(S)-2-azido-3-phenylpropanamido]-N-[1-hydrazinyl-4-methyl-1-oxopentan-2-yl]-N,4-dimethylpentanamide [ No CAS ]
  • 17
  • [ 66866-69-1 ]
  • C39H57N7O7S [ No CAS ]
  • 18
  • [ 66866-69-1 ]
  • C14H28N2O3*C2HF3O2 [ No CAS ]
  • 19
  • [ 66866-69-1 ]
  • [ 115-11-7 ]
  • [ 42807-86-3 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; In 1,4-dioxane; dichloromethane; at 0 - 20℃; for 18h;Sealed tube; 2-Methylpropene (25 g, 446 mmol) was bubbled into DCM (50 mL) at -78C. Then the 2- methylpropene solution was added to a solution of <strong>[66866-69-1](S)-4-methyl-2-(methylamino)pentanoic acid hydrochloride</strong> (500 mg, 2.75 mmol) and H2SO4 (3.68 g, 2 mL, 37.5 mmol) in dioxane (20 mL) at 0C. The reaction mixture was stirred at room temperature for 18 hrs in a sealed tube. The reaction solution was poured into an ice cold aqueous KOH solution (8.4 g in water (30mL)) and the resulting mixture was extracted with DCM (50 mL) twice. The combined organic layer was washed with brine (30 mL) twice, dried over Na2S04 and concentrated in vacuo to afford the crude product ie/t-butyl (2S)-4-methyl-2-(methylamino)pentanoate (Compound AT-1) as a light yellow oil.
With sulfuric acid; In 1,4-dioxane; dichloromethane; at -78 - 20℃; for 18h;Sealed tube; 2-Methylpropene (25 g, 446 mmol) was bubbled into DCM (50 mL) at -78C. Then the 2-methylpropene solution was added to a solution of (S)-4-methyl-2- (methylamino)pentanoic acid hydrochloride (500 mg, 2.75 mmol) and H2S04 (3.68 g, 2 mL, 37.5 mmol) in dioxane (20 mL) at 0C. The reaction mixture was stirred at roomtemperature for 18 hrs in a sealed tube. The reaction solution was poured into an ice coldaqueous KOH solution (8.4 g in water (3OmL)) and the resulting mixture was extractedwith DCM (50 mL) twice. The combined organic layer was washed with brine (30 mL)twice, dried over Na2SO4 and concentrated in vacuo to afford the crude product tert-butyl(2S)-4-methyl-2-(methylamino)pentanoate (Compound AT-i) as a light yellow oil.
With sulfuric acid; In 1,4-dioxane; dichloromethane; at 0 - 20℃; for 18h;Sealed tube; 2-Methylpropene (25 g, 446 mmol) was bubbled into DCM (50 mL) at -78 C. Then the 2-methylpropene solution was added to a solution of <strong>[66866-69-1](S)-4-methyl-2-(methylamino)pentanoic acid hydrochloride</strong> (500 mg, 2.75 mmol) and H2SO4 (3.68 g, 2 mL, 37.5 mmol) in dioxane (20 mL) at 0 C. The reaction mixture was stirred at room temperature for 18 hrs in a sealed tube. The reaction solution was poured into an ice cold aqueous KOH solution (8.4 g in water (30 mL)) and the resulting mixture was extracted with DCM (50 mL) twice. The combined organic layer was washed with brine (30 mL) twice, dried over Na2SO4 and concentrated in vacuo to afford the crude product tert-butyl (2S)-4-methyl-2-(methylamino)pentanoate (Compound AT-1) as a light yellow oil.
  • 20
  • [ 66866-69-1 ]
  • [ 67-63-0 ]
  • isopropyl (2S)-4-methyl-2-(methylamino)pentanoate hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
510 mg With thionyl chloride; In neat (no solvent); for 16h;Reflux; To a solution of <strong>[66866-69-1](S)-4-methyl-2-(methylamino)pentanoic acid hydrochloride</strong> (0.5 g) in i- PrOH (7.8 g, 10 mL) was added thionyl chloride (655 mg, 402 μ) dropwise at room (0389) temperature. The resulting mixture was stirred and refluxed for 16 hrs and then concentrated in vacuo. The residue was basified with saturated aqueous NaHC03 (30 mL) and extracted with DCM (50 mL). The organic layer was washed with brine, dried over Na2S04 and concentrated in vacuo. The residue was salified with HCl/EtOAc (10 mL, 1 mmol/mL) and concentrated to afford isopropyl (2S)-4-methyl-2-(methylamino)pentanoate hydrochloride (510 mg, Compound AU-1) as a white solid.
510 mg With thionyl chloride; for 16h;Reflux; To a solution of <strong>[66866-69-1](S)-4-methyl-2-(methylamino)pentanoic acid hydrochloride</strong> (0.5 g) in i-PrOH (7.8 g, 10 mL) was added thionyl chloride (655 mg, 402 jiL) dropwise at room temperature. The resulting mixture was stirred and refluxed for 16 hrs and then concentrated in vacuo. The residue was basified with saturated aqueous NaHCO3 (30 mL)and extracted with DCM (50 mL). The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was salified with HCIIEtOAc (10 mL, 1 mmol/mL) and concentrated to afford isopropyl (2S)-4-methyl-2-(methylamino)pentanoate hydrochloride (510 mg, Compound AU-i) as a white solid.
510 mg With thionyl chloride; for 16h;Reflux; To a solution of <strong>[66866-69-1](S)-4-methyl-2-(methylamino)pentanoic acid hydrochloride</strong> (0.5 g) in i-PrOH (7.8 g, 10 mL) was added thionyl chloride (655 mg, 402 μL) dropwise at room temperature. The resulting mixture was stirred and refluxed for 16 hrs and then concentrated in vacuo. The residue was basified with saturated aqueous NaHCO3 (30 mL) and extracted with DCM (50 mL). The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was salified with HCl/EtOAc (10 mL, 1 mmol/mL) and concentrated to afford isopropyl (2S)-4-methyl-2-(methylamino)pentanoate hydrochloride (510 mg, Compound AU-1) as a white solid.
  • 21
  • [ 78269-85-9 ]
  • [ 66866-69-1 ]
  • N-trimethylsilylethoxycarbonyl-N-methyl-L-leucine [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With sodium hydrogencarbonate; In water; acetone; at 25℃; (4) At 25C, in a 2L reaction flask equipped with a thermometer,Put 310mL acetone, 310mL water, 62.1g (0.34mol) in sequenceN-methyl-L-leucine hydrochloride,57.1g (0.68mol) sodium bicarbonate, 176.1g (0.68mol)N-[2-(Trimethylsilyl)ethoxycarbonyloxy]succinimide, stir and react overnight at 25C,Add 310mL water and 200mL petroleum ether, stir and extract,Separate the phases, adjust the aqueous phase to weak acidity with 3N hydrochloric acid, add 200mL ethyl acetate to extract the aqueous phase twice, combine the ethyl acetate phases, wash once with saturated sodium chloride, dry with anhydrous sodium sulfate, and concentrateObtain 86.8 g of N-trimethylsilyl ethoxycarbonyl-N-methyl-L-leucine, which is then recrystallized using ethyl acetate petroleum ether71.2g of N-trimethylsilylethoxycarbonyl-N-methyl-L-leucine was obtained, the yield was 72%, the chemical purity was 99.7%, and the chiral purity was 100%.
  • 22
  • [ 113306-55-1 ]
  • [ 66866-69-1 ]
  • N-trimethylsilylethoxycarbonyl-N-methyl-L-leucine [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With sodium hydrogencarbonate; In methanol; water; at 30 - 40℃; (4) At 40C, in a 2L reaction flask equipped with a thermometer, put 828mL methanol, 414mL water, 62.1g (0.34mol) N-methyl-L-leucine hydrochloride, 179.46g (2.04mol) ) Sodium bicarbonate, 474.93g (1.70mol)1-[2-(Trimethylsilyl)ethoxycarbonyloxy]benzotriazole, stirred overnight at 30C, added 310mL water and 200mL petroleum ether, stirred and extracted, and separated phases.The aqueous phase was adjusted to weakly acidic with 3N hydrochloric acid, and 200 mL of ethyl acetate was added to extract the aqueous phase twice. The ethyl acetate phases were combined, washed once with saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated to obtain 91.4 g of N-trimethyl Silylethoxycarbonyl-N-methyl-L-leucine, and then recrystallized with ethyl acetate petroleum ether to obtain 72.2g of N-trimethylsilylethoxycarbonyl-N-methyl-L-leucine,The yield was 73%,The chemical purity is 99.7%, and the chiral purity is 100%.
  • 23
  • [ 13139-15-6 ]
  • [ 66866-69-1 ]
  • 24
  • [ 61-90-5 ]
  • [ 66866-69-1 ]
  • 25
  • [ 53363-89-6 ]
  • [ 66866-69-1 ]
YieldReaction ConditionsOperation in experiment
62.1 g With hydrogenchloride; In dichloromethane; at 15℃; (3) Put 880mL of dichloromethane and 88.3g of N-methyl-Boc-L-leucine into a 2L reaction flask equipped with a thermometer at 15C, stir to dissolve and clear,Pass in hydrogen chloride gas very slowly. As the reaction progresses, the system slowly becomes turbid.A white solid precipitates out. After the raw material has reacted completely, filter it.Obtain 62.1g of N-methyl-L-leucine hydrochloride;
  • 26
  • [ 66866-69-1 ]
  • [ 654071-45-1 ]
  • methyl ((dodec-1-en-5-yloxy)carbonyl)-L-leucinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a stirred solution of dodec-1-en-5-ol lnt-A-1 (12 g,65.57 mmol) in acetonitrile (120 mL) at 0 C was added triethylamine (27 mL, 196.72 mmol) and N,N-disuccinamidyl carbonate (41.9 g, 163.93 mmol) and stirred at room temperature for 16 h. After 16 h, the reaction mixture was evaporated to dryness under reduced pressure. The crude was diluted with ice water (100 mL), extracted with EtOAc (2 x 55 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure to obtain crude residue (5 g, 15.38 mmol). It was taken in DCM (100 mL) added triethylamine (6.4 mL, 46.15 mmol)) and methyl-L-leucinate hydrochloride (4) (5.5 g, 30.76 mmol) at 0 C and stirred at room temperature for 16 h. The progress of the reaction was monitored by TLC. The reaction mixture was quenched with ice water (50 mL) and extracted with DCM (2 x 50 mL). Organic layer was washed with brine solution (30 mL), dried over sodium sulfate and concentrated under reduced pressure. Crude was purified through silica gel (100-200 mesh) column chromatography by eluting with 1% EtOAc in pet ether to afford methyl ((dodec-1-en-5-yloxy)carbonyl)-L-leucinate (5).
 

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