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[ CAS No. 2483-51-4 ]

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Chemical Structure| 2483-51-4
Chemical Structure| 2483-51-4
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Product Details of [ 2483-51-4 ]

CAS No. :2483-51-4 MDL No. :MFCD00191050
Formula : C15H20N2O5 Boiling Point : -
Linear Structure Formula :C15H20O5N2 InChI Key :-
M.W :308.33 g/mol Pubchem ID :7019113
Synonyms :

Safety of [ 2483-51-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2483-51-4 ]

  • Downstream synthetic route of [ 2483-51-4 ]

[ 2483-51-4 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 10065-72-2 ]
  • [ 1142-20-7 ]
  • [ 2483-51-4 ]
YieldReaction ConditionsOperation in experiment
73.1% N-benzyloxycarbonyl-L-alanine (100 g, 0.45 mol) was dissolved in a dried N,N-dimethylformamide (3 L), and 1-hydroxylbenzotriazole (72.6 g, 0.54 mol) and 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (103.3 g, 0.54 mol) were added while stirring. After stirring for reaction for 1 hour, the mixture was subjected to an ice both until the temperature reached 0 C. L-alanine methyl ester (46.2 g, 0.45 mol) and N,N-diisopropyl ethylamine (173.8 g, 1.34 mol) dissolved in an N,N-dimethylformamide (1 L) solution were dropped into the mixture. After dropping, the mixture was stirred under ambient temperature for 10 hours and the solvents were removed by evaporation under reduced pressure. The crude product was dissolved in dichloromethane (2 L) and washed successively with saturated ammonia chloride solution, water and saturated sodium chloride solution. The organic phase was dried with anhydrous sodium sulfate and the solvents were removed by evaporation under reduced pressure. The crude product was re-crystallized by ethyl acetate/petroleum ether to obtain a pure product, which was a white solid I, i.e., Cbz-L-Ala-L-Ala-OMe (101 g; Yield, 73.1%).
73.1% [0082] N-benzyloxycarbonyl-LAla (100g, 0.45mol) were dissolved in N,N-dimethylformamide (3L). 1-hydroxylbenzotriazole (HOBt, 72.6g, 0.54mol) and 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC, 103.3g, 0.54mol) were added when stirring. After reacting for 1 hour under stirring, the mixture was cooled to 0C in an ice bath and L-Ala methyl ester (46.2g, 0.45mol) and N,N-diisopropylethylamine (173.8g, 1.34mol) in the N,N-dimethylformamide solution (1L) was dropped into the mixture. After dropping, the mixture was stirred under ambient temperature for 10 hours. The solvents were removed by evaporation under reduced pressure. The crude product was dissolved in dichloromethane (2L) and washed subsequently by saturated ammonium chloride solution, water and saturated sodium chloride solution. The organic phase was dried by anhydrous sodium sulphate. After removing the solvents by evaporation under reduced pressure, the crude product was recrystallized to obtain a white solid I (101g, Yield 73.1%).
73.1% N-benzyloxycarbonyl-L-alanine (100 g, 0.45 mol) was dissolved in a dried N,N-dimethylformamide (3 L), and 1-hydroxylbenzotriazole (72.6 g, 0.54 mol) and 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (103.3 g, 0.54 mol) were added while stirring. After stirring for reaction for 1 hour, the mixture was subjected to an ice bath until the temperature reached 0 C. L-alanine methyl ester (46.2 g, 0.45 mol) and N,N-diisopropyl ethylamine (173.8 g, 1.34 mol) dissolved in an N,N-dimethylformamide (1 L) solution were dropped into the mixture. After dropping, the mixture was stirred under ambient temperature for 10 hours and the solvents were removed by evaporation under reduced pressure. The crude product was dissolved in dichloromethane (2 L) and washed successively with saturated ammonia chloride solution, water and saturated sodium chloride solution. The organic phase was dried with anhydrous sodium sulfate and the solvents were removed by evaporation under reduced pressure. The crude product was re-crystallized by ethyl acetate/petroleum ether to obtain a pure product, which was a white solid I, i.e., Cbz-L-Ala-L-Ala-OMe (101 g; Yield, 73.1%).
  • 2
  • [ 2483-51-4 ]
  • [ 2483-52-5 ]
YieldReaction ConditionsOperation in experiment
85% With hydrazine; In methanol; at 20℃; for 18h; A solution of <strong>[2483-51-4]methyl ((benzyloxy)carbonyl)-L-alanyl-L-alaninate</strong> (2 g,6.4 mmol) in MeOH (50 mL) was treated with the drop wise addition of hydrazine (2.12 mL, 64 mmol). The reaction was stirred at RT for 18 h. MeOH and excess hydrazine were removed in vacuo and remaining white solid was collected by vacuum filtration and washed with EtOAc (1.68 g, 5.4 mmol). Yield: 85% ‘H NMR (DMSO, 400 MHz) ö 1.18 (s, 3H), 1.19 (s, 3 H), 4.04-4.11 (m, 1 H), 4.20-4.26 (m, 2H), 4.97-5.07 (m, 2H), 7.29-7.40 (m, 5H), 7.40-7.48 (d, 1H), 7.87-7.93 (d, 1H), 9.05 (s, 1H).
  • 4
  • [ 2483-51-4 ]
  • [ 16012-70-7 ]
YieldReaction ConditionsOperation in experiment
92.2% With water; lithium hydroxide; In tetrahydrofuran; at 0℃; for 10h; <strong>[2483-51-4]Cbz-L-Ala-L-Ala-OMe</strong> (100 g, 0.34 mol) was dissolved in a mixed solution of tetrahydrofuran (2 L) and water (1 L) and cooled to 0 C. 1 mol/L lithium hydroxide solution (400 mL) was dropped to the mixture and then stirred and reacted for 10 hours. Concentrated hydrochloric acid was dropped to the mixture to neutralize its pH to below 6. Tetrahydrofuran was removed by evaporation under reduced pressure. The residual water phase was extracted by dichloromethane (1 L*3). The organic phase was dried with anhydrous sodium sulfate and removed by evaporation under reduced pressure to obtain a white solid II, i.e., Cbz-Ala-Ala-OH (88 g; Yield, 92.2%).
92.2% With water; lithium hydroxide; In tetrahydrofuran; at 0℃; for 10h; [0084] N-(N-benzyloxycarbonyl-L-alanyl)-L-Ala methyl ester (100g, 0.34mol) were dissolved in a mixed solution of tetrahydrofuran (2L) and water (1L). The mixture was cooled to 0C and 1M lithium hydroxide solution (400mL) were dropped into the mixture. The resultant mixture was stirred for reaction for 10 hours. Concentrated hydrochloric acid was dropped to adjust the pH to be less than 6. Most of tetrahydrofuran were removed by rotary evaporation. The residual water phase was extracted by dichloromethane (1L*3). The organic phase was dried by anhydrous sodium sulphate. A white solid II was obtained after vaporizing and drying under reduced pressure (88g; Yield, 92.2%).
92.2% With water; lithium hydroxide; In tetrahydrofuran; at 0℃; for 10h; <strong>[2483-51-4]Cbz-L-Ala-L-Ala-OMe</strong> (100 g, 0.34 mol) was dissolved in a mixed solution of tetrahydrofuran (2 L) and water (1 L) and cooled to 0 C. 1 mol/L lithium hydroxide solution (400 mL) was dropped to the mixture and then stirred and reacted for 10 hours. Concentrated hydrochloric acid was dropped to the mixture to neutralize its pH to below 6. Tetrahydrofuran was removed by evaporation under reduced pressure. The residual water phase was extracted by dichloromethane (1 L*3). The organic phase was dried with anhydrous sodium sulfate and removed by evaporation under reduced pressure to obtain a white solid II, i.e., Cbz-Ala-Ala-OH (88 g; Yield, 92.2%).
With lithium hydroxide; In tetrahydrofuran; water; at 0℃; for 3h; General procedure: The dipeptide 12a-v (1.0 eq) was dissolved in THF:H2O (4:1, 10 mL) and LiOH (1.2 equiv) was added at 0 C. The mixture was stirred at 0 C for 3 hours before acidifying with 1 M HCl (2 mL) to < pH 3. The aqueous phase was extracted with EtOAc (3 X 5 mL), dried over sodium sulfate, filtered, and concentrated to yield 13a-v, which were confirmed by MS then carried directly into the final step.

  • 5
  • [ 2483-51-4 ]
  • [ 24326-09-8 ]
YieldReaction ConditionsOperation in experiment
With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; under 2250.23 Torr; for 1h; General procedure: In a 3-neck round bottom flaskequipped with a septum, a thermometer and an adapter for a balloon with argon, Cbz-aminoacid(1.0 equiv., 5.0 mM) and N-ethylpiperidine (1.1 equiv., 5.5 mM) were dissolved in anhydrous methylenechloride (25 mL) and cooled to 10 C. Ethyl chloroformate (1.1 equiv., 5.5 mM) was added at the sametemperature, and the mixture protected from ingress of moisture was stirred for 2 h. Hydrochlorideof methyl L-alaninate or methyl glycinate (1.0 equiv., 5.0 mM) was dissolved in the second ask inanhydrous methylene chloride (10 mL) and cooled to 0 C, and then N-ethylpiperidine (1.0 equiv.,5.0 mM) was added. The whole volume of the second flask was immediately transferred to a 3-neckround bottom flask with the help of syringe, and additional N-ethylpiperidine (1.0 equiv., 5.0 mM)was added. The solution was stirred at the same temperature for 2 h and then left at 5 C overnight.After that, the reaction mixture was quenched with water (35 mL). The aqueous phase was extractedwith methylene chloride (3 15 mL). Combined organic phases were washed with 2M HCl solution(3 10 mL), water (10 mL), saturated sodium hydrogen carbonate solution (3 10 mL), and brine(10 mL) and dried over anhydrous sodium sulfate. After filtration, the solvent was removed underreduced pressure to give Cbz-amino dipeptide esters. The crude Cbz-amino dipeptide esters werehydrogenated with 60 mL of methanol and 10% Pd/C as a catalyst (0.5 g of Pd/C per 3 mM ofintermediate dipeptide esters) at room temperature. The reactor (250 mL capacity Parr reactor) waspressurized with hydrogen to 3 bars at ambient temperature. Reactor pressure remained unchangedduring the reaction period of 1 h. After releasing the pressure, the catalyst was removed by filtrationthrough Celite, and the solvent was removed under reduced pressure. The crude amino dipeptideesters were placed into a 250 mL round-bottomed flask equipped with an egg-shaped, Teflon-coated magnetic stirring bar and a reflux condenser, and toluene (100 mL) containing 5 mL of acetic acidwas added. The reaction mixture was stirred and refluxed for 2 h, then the reflux condenser wasremoved, and the amount of the solvent was reduced to 10% at atmospheric pressure. The remainingsolvent was removed under reduced pressure and the residue was recrystallized from propane-2-ol.Pure piperazine-2,5-diones 3-5 were dried at 40 C under reduced pressure.
  • 6
  • [ 2483-51-4 ]
  • (+/-)-<i>cis</i>-3,6-dimethyl-piperazine-2,5-dione [ No CAS ]
  • 9
  • [ 2483-51-4 ]
  • [ 95205-40-6 ]
  • [ 95205-39-3 ]
  • 11
  • [ 1142-20-7 ]
  • [ 2491-20-5 ]
  • [ 2483-51-4 ]
YieldReaction ConditionsOperation in experiment
90% With N-[2-(4-sulphonatephenylamino)-4-methoxy-1,3,5-triazin-6-yl]-4-methylmorpholinium inner salt; sodium hydrogencarbonate; In water; for 5h;Product distribution / selectivity; Example 19. A round-bottomed flask was charged with Z-Ala-OH (0.223 g, 0.001 mol), H-Ala-OMe x HCl (0.140 g, 0.001 mol), SPMT x 5H2O (0.471 g, 0.001 mol) and NaHCO3 (0.168 g, 0.002 mol). Water (10 ml) was added to the flask and the mixture was stirred using a magnetic stirrer. During the reaction, a formation of white precipitate was observed. After 5 hours, the precipitate was filtered off and dried in the air. Z-Ala-Ala-OMe (0.278 g, 90% yield) was obtained in the form of a white powder, having the m.p. of 93-94C (lit. 106-108C). The results of NMR analysis of the obtained compound are as follows: 1H NMR (acetone-d6) δ = 1.341 (d, J = 7 Hz, CH3, 3H); δ = 1.380 (d, J = 7 Hz, CH3, 3H); 3.673 (s, CH3, 3H); 4.240 (dp, J = 7.25 Hz, J = 2 Hz, CH, 1H); 4.435 (dp, J = 7.5 Hz, J = 1 Hz, CH, 1H); 5.077 (d, J = 1.5 Hz, CH2, 2H); 6.482 (m, NH, 1H); 7.267-7.417 (m, CArH, 5H); 7.536 (m, NH, 1H) [ppm].
52% With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at 0 - 20℃; General procedure: To a solution of ((benzyloxy)carbonyl)-L-phenylalanine (0.72 g, 2.4 mmol, 1.0 eq) andN-methylmorpholine (0.97 g, 9.6 mmol, 4.0 eq) in anhydrous THF was added isobutylchloroformate (0.49 g, 3.6 mmol, 1.5 eq) at 0 C. The methyl L-alaninate hydrochloride(0.33 g, 2.4 mmol, 1.0 eq) was then added and the reaction was allowed to warm slowly toroom temperature overnight. The next day the reaction mixture was diluted with EtOAc(25 mL) and washed in succession with 1.0 M HCl (50 mL), 5% sodium carbonate solution(50 mL), brine (50 mL), then dried over sodium sulfate before filtering and concentrating invacuo. The residue was recrystallized in a DCM:Hexanes solution and filtered, yielding12g as a white crystalline solid (0.61 g, 1.6 mmol, 66%).
  • 12
  • [ 2491-20-5 ]
  • [ 26607-52-3 ]
  • [ 2483-51-4 ]
  • 13
  • [ 2491-20-5 ]
  • Z-alanyl-p-toluenesulfonate [ No CAS ]
  • [ 2483-51-4 ]
  • 14
  • [ 2491-20-5 ]
  • [ 122751-37-5 ]
  • [ 2483-51-4 ]
  • 15
  • (Z-L-Ala-L-Ala-SCH2CH2)2O [ No CAS ]
  • [ 2483-51-4 ]
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