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[ CAS No. 1142-20-7 ] {[proInfo.proName]}

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Chemical Structure| 1142-20-7
Chemical Structure| 1142-20-7
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Quality Control of [ 1142-20-7 ]

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Product Details of [ 1142-20-7 ]

CAS No. :1142-20-7 MDL No. :MFCD00002640
Formula : C11H13NO4 Boiling Point : -
Linear Structure Formula :HO2CCH(NHCOOCH2C6H5)CH3 InChI Key :TYRGLVWXHJRKMT-QMMMGPOBSA-N
M.W : 223.23 Pubchem ID :736104
Synonyms :
(S)-2-(Benzyloxycarbonylamino)propanoic acid;L-Alanine, N-carboxy-, N-benzyl ester (6CI,7CI);N-[(Benzyloxy)carbonyl]-L-alanine
Chemical Name :((Benzyloxy)carbonyl)-L-alanine

Safety of [ 1142-20-7 ]

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

Application In Synthesis of [ 1142-20-7 ]

* 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 [ 1142-20-7 ]

[ 1142-20-7 ] Synthesis Path-Downstream   1~17

  • 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
  • [ 1142-20-7 ]
  • [ 63060-94-6 ]
  • [ 98807-09-1 ]
  • 3
  • [ 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%).
  • 5
  • [ 1142-20-7 ]
  • [ 2011-66-7 ]
  • [ 58662-82-1 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; sodium hydrogencarbonate; In tetrahydrofuran; Petroleum ether; (a) 53.6 g of carbobenzoxy-L-alanine are dissolved in 400 ml of dry tetrahydrofuran, the solution is treated dropwise with 30 g of thionyl chloride while cooling with ice and the mixture is stirred for 1 hour in the cold. A solution of 54 g (0.2 mol) of <strong>[2011-66-7]2-amino-5-nitro-2'-chlorobenzophenone</strong> in 150 ml of dry tetrahydrofuran is subsequently added dropwise thereto rapidly, whereupon the mixture is stirred at room temperature for 24 hours. The solution obtained is concentrated, the residue is treated with ice and 10 percent sodium bicarbonate solution and extracted with methylene chloride. The organic solution is dried over sodium sulphate and evaporated. The residue is treated with dry ether, left to crystallize for 1 hour and then filtered while rinsing with ether/petroleum ether (1:1). After drying, there is obtained (S)-benzyl-[1-[[2-(o-chlorobenzoyl)-4-nitrophenyl]carbamoyl]ethyl]carbamate of melting point 143-145; [alpha]25 D =18 (1 percent solution in methylene chloride).
  • 6
  • [ 1142-20-7 ]
  • [ 2338-18-3 ]
  • phenylmethyl [2-[(2,3-dihydro-1H-inden-2-yl)amino]-1R-methyl-2-oxoethyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 20 phenylmethyl [2-[(2,3-dihydro-1H-inden-2-yl)amino]-1R-methyl-2-oxoethyl]carbamate STR29 (Z-(D)Ala-NH-2Indane) The title compound was prepared from Z-(D)Alanine (10 g, 44.8 mmol) and 2-amino indane hydrochloride (7.6 g, 44.8 mmol) by the method of Example 8. After workup, the crude solid was washed liberally with Et2 O to give 12.35 g of the white solid title material.
  • 7
  • [ 1142-20-7 ]
  • [ 2011-66-7 ]
  • [ 80080-94-0 ]
YieldReaction ConditionsOperation in experiment
With phosphorus pentachloride; In tetrahydrofuran; toluene; 82 g of carbobenzoxy-L-alanine are dissolved in 100 ml of absolute tetrahydrofuran, the solution is cooled to -40 C and treated with 80 g of phosphorus pentachloride. The mixture is stirred at -30 C for 20 minutes and subsequently added to a shaken solution of 80 g of <strong>[2011-66-7]2-amino-5-nitro-2'-chlorobenzophenone</strong> in 100 ml of absolute tetrahydrofuran. The solution is concentrated on a rotary evaporator at 50-60 C, treated twice with toluene and evaporated each time. By crystallisation of the residue from ether, there is obtained (-)-benzyl-[1-[{2-(o-chlorobenzoyl)4-nitrophenyl}carbamoyl]-ethyl]carbamate which melts at 147 C and exhibits a rotation of [alpha]25D =-18.2 (in methylene chloride, 1%).
  • 8
  • [ 1142-20-7 ]
  • [ 73101-74-3 ]
  • [ 1254122-50-3 ]
  • 9
  • [ 1142-20-7 ]
  • [ 78603-91-5 ]
  • 10
  • [ 1142-20-7 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • N-(9-fluorenylmethoxycarbonyl)-(L)-5-hydroxy-norvaline-1-allyl ester [ No CAS ]
  • [ 73731-37-0 ]
  • [ 77128-73-5 ]
  • C49H72N8O12 [ No CAS ]
  • 11
  • [ 1142-20-7 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • N-(9-fluorenylmethoxycarbonyl)-(L)-5-hydroxy-norvaline-1-allyl ester [ No CAS ]
  • [ 73731-37-0 ]
  • [ 77128-73-5 ]
  • C51H76N8O11 [ No CAS ]
  • 12
  • [ 1142-20-7 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • N-(9-fluorenylmethoxycarbonyl)-(L)-5-hydroxy-norvaline-1-allyl ester [ No CAS ]
  • [ 35661-40-6 ]
  • [ 73731-37-0 ]
  • [ 77128-73-5 ]
  • C53H72N8O12 [ No CAS ]
  • 13
  • [ 1142-20-7 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • N-(9-fluorenylmethoxycarbonyl)-(L)-5-hydroxy-norvaline-1-allyl ester [ No CAS ]
  • [ 35661-40-6 ]
  • [ 73731-37-0 ]
  • [ 77128-73-5 ]
  • C53H72N8O12 [ No CAS ]
  • 14
  • [ 1142-20-7 ]
  • [ 68858-20-8 ]
  • [ 35661-39-3 ]
  • N-(9-fluorenylmethoxycarbonyl)-(L)-5-hydroxy-norvaline-1-allyl ester [ No CAS ]
  • [ 35661-40-6 ]
  • [ 73731-37-0 ]
  • [ 77128-73-5 ]
  • C52H70N8O12 [ No CAS ]
  • 15
  • [ 1142-20-7 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • N-(9-fluorenylmethoxycarbonyl)-(L)-5-hydroxy-norvaline-1-allyl ester [ No CAS ]
  • [ 35661-40-6 ]
  • [ 73731-37-0 ]
  • [ 77128-73-5 ]
  • C55H76N8O12 [ No CAS ]
  • 16
  • [ 1142-20-7 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • N-(9-fluorenylmethoxycarbonyl)-(L)-5-hydroxy-norvaline-1-allyl ester [ No CAS ]
  • [ 77128-73-5 ]
  • [ 197458-39-2 ]
  • C54H74N8O12 [ No CAS ]
  • 17
  • [ 940301-35-9 ]
  • [ 1142-20-7 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • N-(9-fluorenylmethoxycarbonyl)-(L)-5-hydroxy-norvaline-1-allyl ester [ No CAS ]
  • [ 77128-73-5 ]
  • C51H76N8O12 [ No CAS ]
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