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[ CAS No. 5557-81-3 ] {[proInfo.proName]}

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Chemical Structure| 5557-81-3
Chemical Structure| 5557-81-3
Structure of 5557-81-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5557-81-3 ]

CAS No. :5557-81-3 MDL No. :MFCD07809339
Formula : C10H14ClNO2 Boiling Point : -
Linear Structure Formula :C10H13O2N*HCl InChI Key :-
M.W : 215.68 Pubchem ID :-
Synonyms :

Safety of [ 5557-81-3 ]

Signal Word: Class:
Precautionary Statements: UN#:
Hazard Statements: Packing Group:

Application In Synthesis of [ 5557-81-3 ]

* 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 [ 5557-81-3 ]

[ 5557-81-3 ] Synthesis Path-Downstream   1~88

  • 1
  • [ 2188-18-3 ]
  • [ 5557-81-3 ]
  • [ 2132-52-7 ]
  • 2
  • [ 5557-81-3 ]
  • (S)-3-tert-Butoxycarbonylamino-N-(2,4-dimethoxy-benzyl)-succinamic acid; compound with dicyclohexyl-amine [ No CAS ]
  • (S)-2-[(S)-3-tert-Butoxycarbonylamino-3-(2,4-dimethoxy-benzylcarbamoyl)-propionylamino]-propionic acid benzyl ester [ No CAS ]
  • 3
  • [ 13528-93-3 ]
  • [ 5557-81-3 ]
  • [ 139215-48-8 ]
  • 5
  • [ 1149-26-4 ]
  • [ 5557-81-3 ]
  • [ 118234-89-2 ]
  • 6
  • [ 1117-96-0 ]
  • [ 710-11-2 ]
  • [ 5557-81-3 ]
  • [ 82717-95-1 ]
  • [ 93841-86-2 ]
  • 7
  • [ 1170-76-9 ]
  • [ 5557-81-3 ]
  • [ 132970-10-6 ]
  • 8
  • [ 64920-29-2 ]
  • [ 5557-81-3 ]
  • [ 82717-95-1 ]
  • 9
  • [ 23680-31-1 ]
  • [ 5557-81-3 ]
  • [ 98628-22-9 ]
  • 10
  • [ 5557-81-3 ]
  • [ 84708-53-2 ]
  • [ 84708-55-4 ]
  • 11
  • [ 5557-81-3 ]
  • [ 139517-78-5 ]
  • 3-<3-(2-azidoethyl)-4-methoxyphenyl>-N-tert-butoxycarbonyl-O-methyl-(S)-tyrosyl-(S)-alanine benzyl ester [ No CAS ]
  • 12
  • [ 777-52-6 ]
  • [ 5557-81-3 ]
  • [ 840506-34-5 ]
  • 13
  • [ 1479-10-3 ]
  • [ 5557-81-3 ]
  • [ 840506-36-7 ]
  • 14
  • [ 5557-81-3 ]
  • [ 152568-35-9 ]
  • [ 671753-67-6 ]
  • 15
  • [ 5557-81-3 ]
  • 2-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-methyl-propionic acid pentafluorophenyl ester [ No CAS ]
  • [ 203636-23-1 ]
  • 16
  • [ 5557-81-3 ]
  • [ 671753-65-4 ]
  • [ 671753-70-1 ]
  • 17
  • [ 5557-81-3 ]
  • [ 770-12-7 ]
  • [ 183370-70-9 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at -75 - 30℃; for 3h; Example 3; Preparation of gemcitabine- [phenyl(benzoxy-L-alaninyl)] phosphate via 4-N-3'-0- bis(teri-butoxycarbonyl) gemcitabine: To a suspension of <strong>[5557-81-3]L-alanine benzyl ester hydrochloride</strong> (19.7 gms, 0.0914 mol) in DCM (200 ml), was charged dichloro phenyl phosphate (19.6 gms, 0.0928 mol) at 25- 30C and cooled to -70C to about -75C. TEA (18.5 gms, 0.1825 mol) was added to the reaction mixture at -70C to about -75C, stirred at the same temperature for 1 hr and at 25-30C for 2hrs and concentrated the reaction mass under reduced pressure. The obtained residue was treated with DIPE (200 ml), filtered and concentrated under reduced pressure and stored under nitrogen at 0-7C. To a stirred mixture of 4-N-3 ' -O-bis( rt-butoxycarbonyl) gemcitabine (20 gms) in THF (200 ml), was added the Pro Tide intermediate prepared above taken in 200 ml THF under nitrogen atmosphere and cooled the resulting solution to -5 to 5C. Charged 1M t-BuMgCl (10 gms, 0.0863 mol), raise the temperature to 25-30C and stirred for 30mins. After reaction completion the reaction mass was quenched in to water (200 ml) and extracted with EtOAc (300 ml). The organic layer was washed with 8% NaHC03, water and finally with 20% brine solution. The organic layer separated, dried over sodium sulfate and concentrated under reduced pressure to obtain a residue. The obtained residue was taken up in DCM (160 ml) and added TFA (160 ml) at -2 to 2C. Maintained the reaction mass at 5-10C for 2-3 hrs and quenched in to 10% sodium carbonate solution (2 Lit) at below 15C. Extracted with EtOAc (800 ml), dried the organic layer over sodium sulfate and evaporated under reduced pressure. The obtained residue was slurried in DCM: heptane mixture to obtain the title compound (21.6 gms; 85%). Purity by HPLC: 99.68% (mixture of both diastereomers in approximately 1 : 1 ratio).
With triethylamine; In dichloromethane; at -78 - 35℃; for 3h; To a stirred mixture of <strong>[5557-81-3]L-alanine benzyl ester hydrochloride</strong> (100 gms) in methylene chloride (1 lit) was added phenyl dichlorophosphate (77 ml) at 25-35C and the resulting mixture was cooled to -70C to -78C, added triethyl amine (130.5 ml) and stirred for I hrs at same temperature. Reaction mass temperature was raised to 25- 35C and allowed to stir for 2hrs. After reaction completion, concentrated the reaction mass under vacuum at below 35C to obtain residue. To the obtained residue was added diisopropyl ether (2 lit) at 25-35C and stirred for 30 mm at same temperature. Filtered the reaction mass and washed with diisopropyl ether (500 ml) followed by concentrating the filtrate under vacuum at below 35C to obtain phenyl(benzoxy-L-alaninyl)-phosphorochloridate. The obtained compound was dissolved in methylene chloride (1 lit) at 25-35C and cooled to -5C to -10C. To the reaction mass Pentafluorophenol (85.5 gms), triethyl amine (65.2 ml) was added at same temperature and stirred for 2hrs. After reaction completion, concentrated the reaction mass under vacuum at below 35C and charged ethyl acetate (1 lit) at 25-35C and stirred for 30 mm at same temperature. Filtered the solids and washed with ethyl acetate (1 lit). To the filtrate was given water (1 lit), 10% sodium carbonate (2x1 lit), brine (1 lit) washings and dried the organic layer with anhydrous sodium sulphate, concentrated under vacuum at 35-45C to obtain diastereoisomeric mixture of title compound as a white colored semi solid.Yield: 210 gmsChiral Purity by HPLC (% area): 33.74:66.26% (Rp: Sp)
With triethylamine; at -78 - 20℃; for 2.18333h; Triethylamine (1.1 mL) was added at -78 C. to a mixture of phenyl dichlorophosphate (600 muL), <strong>[5557-81-3]L-alanine benzyl ester hydrochloride</strong> (864 mg) and methylene chloride (20 mL) which was then stirred at room temperature for 2 hours and 11 minutes. The solvent was distilled off under reduced pressure. Diethyl ether was added to the resulting residue, and the insoluble matter was separated by filtration. The solvent was distilled off under reduced pressure to give (2S)-benzyl 2-(((RS)-chloro(phenoxy)phosphoryl)amino)propanoate as a crude product.
With triethylamine; In dichloromethane; at -78 - 35℃; for 3h; To a stirred mixture of <strong>[5557-81-3]L-alanine benzyl ester hydrochloride</strong> 1 (100 g) in methylene chloride (1 L) was added phenyl dichlorophosphate 2 (77 mL) at 25-35C and the resulting mixture was cooled to -70C to -78C, triethylamine (130.5 mL) was added and the mixture was stirred for 1 hour at same temperature. Reaction mass temperature was raised to 25-35C and allowed to stir for 2 hours. After reaction completion, concentrated the reaction mass under vacuum at below 35C to obtain residue. To the obtained residue was added diisopropyl ether (2 L) at 25-35C and stirred for 30 min at same temperature. Filtered the reaction mass and washed with diisopropyl ether (500 mL) followed by concentrating the filtrate under vacuum at below 35C to obtain phenyl-(benzoxy-L-alaninyl)-phosphorochloridate 3. The obtained compound was dissolved in methylene chloride (1 L) at 25-35C and cooled to -5C to -10C. To the reaction mass pentafluorophenol 4 (85.5 g), triethylamine (65.2 mL) were added at same temperature and stirred for 2hrs. After reaction completion, concentrated the reaction mass under vacuum at below 35C and charged ethyl acetate (1 L) at 25-35C and stirred for 30 min at same temperature. Filtered the solids and washed with ethyl acetate (1 L). To the filtrate was given water (1 L), 10% sodium carbonate (2x1 L), brine (1 L) washings and dried the organic layer with anhydrous sodium sulphate, concentrated under vacuum at 35- 45C to obtain diastereoisomeric mixture of title compound 5 as a white colored semi solid.
With triethylamine; In dichloromethane; at -78 - 20℃; for 1h; 2.1 g of phenol dichlorophosphate and 2.2 g of <strong>[5557-81-3]L-alanine benzyl ester hydrochloride</strong> were dissolved in 30 mL of anhydrous dichloromethane and cooled to -78 C.A solution of 2 ml of triethylamine dissolved in 20 mL of anhydrous dichloromethane was added dropwise with stirring.The drop rate was controlled to maintain the reaction temperature -78 C. After the addition,The reaction temperature was allowed to rise to room temperature and stirring was continued for 1 hour. The solvent was distilled off under reduced pressure.30 ml of anhydrous diethyl ether was added to the residue and the mixture was filtered. The filtrate was evaporated to dryness under reduced pressure.Intermediate ii-1 was obtained and used directly in the next step.
14.1 g With triethylamine; In dichloromethane; at -70 - 20℃; for 1h; To a -70C solution containing 12.4 g (58.68 mmol) of phenyl phosphorodichloridate and L-alanine benzyl ester HCI (12.7 g, 58.68 mmol, 1.00 eq) in 15 mL of DCM was added 16.3 mL (1 17.36 mmol, 2.00 eq) of TEA in DCM (5 mL) over 0.5 h. The reaction mixture was slowly warmed to 20C and stirred for an additional 0.5 h. The mixture was stirred for 4h then concentrated and filtered. The filter cake was washed with ether and the filtrate was concentrated and the residue was purified by silica gel chromatography (Petroleum Ether : MTBE = 5:1 to 1 :1) to afford Int 7-1 (14.10 g) as a colorless oil. 1H NMR (400 MHz) CDCI3 d 7.31-7.41 (m, 1 H), 7.20-7.28 (m, 1 H), 5.21 (d, J=6.6 Hz, 1 H), 4.16-4.43 (m, 1 H), 1.52 ppm (dd, J=6.8, 2.4 Hz, 1 H).

  • 18
  • [ 5557-81-3 ]
  • [ 772-79-2 ]
  • [ 840506-40-3 ]
YieldReaction ConditionsOperation in experiment
Glassware and molecular sieves were dried in a 900C oven for 24 hours before use. To a solution of <strong>[5557-81-3]L-alanine benzyl ester hydrochloride</strong> (Ig, 0.0046 mol) in anhydrous dichloromethane (3 ml) in a flask containing molecular sieves was added 4- chlorophenyldichlorophosphate (0.54 ml, 0.0033 mol). The mixture was stirred at -10 0C under argon for 10 minutes, then a solution of anhydrous triethylamine (0.92 ml, 0.0066 mol) in anhydrous dichloromethane (2 ml) was added slowly. The reaction mixture was stirred at -10 0C for 2 hours, the solid precipitated in the reaction was filtered and the filtrate was evaporated under reduced pressure. The residue was washed with ether and the filtrate collected was evaporated under reduced pressure to give 1, which was made up as a stock solution in anhydrous tetrahydrofuran for further reaction.
  • 19
  • [ 31651-76-0 ]
  • [ 5557-81-3 ]
  • [ 906670-24-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at -78 - 20℃;Inert atmosphere; Example 1 [Show Image] 3g naphtol were loaded into a 3-neck flask and dissolved in Et2O (60 mL) under N2. To the solution was added POCl3 (1 eq.) and the resulting solution cooled to -78 C. To the cold solution was added drop wise (over approx. 15min.) Et3N (1 eq.). The reaction was allowed to reach rt overnight and then the white solid was filtered off washing with Et2O and avoiding contact with moisture. The combined ethereal phases were concentrated in vacuum and the residue re-dissolved in CH2Cl2 (120mL) under N2. To the solution was added <strong>[5557-81-3]L-alanine benzyl ester hydrochloride</strong> (1 eq.) and the mixture cooled to -78 C. To this was then added drop wise (over approx. 45min) Et3N (1 eq.) and the reaction allowed to reach rt overnight. The solvent was removed in vacuum, avoiding contact with moisture and the residue passed through dry silica-gel eluting with EtOAc/heptane:70/30 and protecting the collected fractions from moisture. The fractions containing the product were concentrated in vacuum avoiding contact with moisture and the residue dissolved in dry THF as to obtain a standard solution of approx. concentration used as such in the next reaction.
With triethylamine; In dichloromethane; at -78 - 20℃;Inert atmosphere; Example 13g of 1-naphthol were loaded into a 3 -neck flask and dissolved in Et20 (60 mL) under N2. To the solution was added POCI3 (1 eq.) and the resulting solution cooled to -78C. To the cold solution was added dropwise (over approx. 15min.) Et3N (1 eq.). The reaction was allowed to reach room temperature overnight and then the white solid was filtered off, washed with Et20 while avoiding contact with moisture. The combined ether phases were concentrated in vacuum, the residue re-dissolved in CH2C12 (120mL) under N2. To this solution was added <strong>[5557-81-3]L-alanine benzyl ester hydrochloride</strong> (1 eq.) and the mixture cooled to -78 C. To this was then added dropwise (over approx. 45min) Et3N (1 eq.). The reaction was allowed to reach room temperature overnight. The solvent was removed in vacuum, avoiding contact with moisture and the residue passed through dry silica-gel eluting with EtO Ac/heptane: 7/3. The fractions containing the product were concentrated in vacuum avoiding contact with moisture and the residue dissolved in dry THF to obtain a standard solution of approximate concentration used as such in the next reaction
With triethylamine; In dichloromethane; at -78 - 20℃; for 6h; Step A. (S)-Benzyl 2-aminopropanoate hydrochloride (Chem Impex, 0.66 g, 3.06 mmol) and naphthalen-l-yl phosphorodichloridate prepared in Example 3 Step A (0.8 g, 3.06 mmol) was suspended in anhydrous DCM (15 mL). The reaction was cooled to -78 C. Triethylamine (619 mg, 852 mu, 6.12 mmol) was added dropwise. The reaction mixture was stirred at -78 C for 1 h, then warmed up to room temperature and stirred for 5 h. The solvent was removed, and the residue was washed with dry ethyl ether and filtered. The filtrate was concentrated to give crude (2S)- benzyl 2-(chloro(naphthalen-l-yloxy)phosphorylamino)propanoate as a light yellow oil (1 g, 81%) and used without further purification.
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -80 - 20℃; To 1-naphthol (1.0 eq., 69.4 mmol, 10.0 g) in diethylether (250 ml) was added phosphorus oxychloride (1.0 eq., 69.4 mmol, 6.5 ml) and the solution was cooled to -78C. Dry JV,JV-diisopropylethylamine (DIPEA; 1.0 eq., 69.4 mmol, 12.1 ml) was added and the resulting solution was left to warm to room temperature overnight. The white slurry was filtered under an inert atmosphere and all volatiles were removed to give A as a colorless liquid that was used without further purification in the next step.A solution of A (1.0 eq., 4.6 mmol, 1.0 g) and 2-amino-propionic acid benzyl ester hydrochloride (1.0 eq., 4.6 mmol, 1.2 g) in CH2Cl2 (40 ml) was cooled down to -800C. Dry DIPEA (2.0 eq., 9.3 mmol, 1.6 ml) was added dropwise. After 1 hour the reaction was warmed up to room temperature. Stirring was continued for 1 more hour and the solvent was removed under reduced pressure. Dry diethylether was added and the precipitate was filtered of and washed twice with dry diethylether under an argon atmosphere. The filtrate was evaporated to dryness to give B which was stored as a 0.97 M solution in tetrahydrofuran (THF) at -18C.To a solution of C (1.0 eq., 0.59 mmol, 150 mg) in dry THF (6 ml) was added t- ButylMgCl (1.5 eq., 0.89 mmol, 521 mul, 1.7 M solution in THF) at room temperature. A solution of B (1.4 eq., 0.83 mmol, 852 mul, 0.97 M solution in THF) was added dropwise and the mixture was stirred at room temperature for 2.5 hours. Thirty drops of saturated aqueous NH4Cl were added and the reaction mixture was evaporated on silica, then purified by column chromatography (0-5% methanol in CH2Cl2) to give 1 (74 mg, yield = 19%, purity = 96%) as a mixture of diastereomers. 1H NMR (400MHz, DMSO-J6) delta ppm 0.39 - 0.61 (m, 3 H) 1.01 - 1.12 (m, 1 H) 1.18 - 1.33 (m, 3 H) 3.88 - 4.09 (m, 3 H) 4.16 - 4.31 (m, 1 H) 4.31 - 4.42 (m, 1 H) 4.96 - 5.16 (m, 2 H) 5.35 - -- 5.49 (m, 2 H) 5.95 (s, 1 H) 6.25 - 6.37 (m, 1 H) 7.26 - 7.35 (m, 5 H) 7.36 - 7.62 (m, 5 H) 7.74 (d, J=8.02 Hz, 1 H) 7.95 (d, J=7.82 Hz, 1 H) 8.11 (t, J=7.92 Hz, 1 H) 11.31 (br. s., 1 H). LC-MS: R1 = 2.21 min, m/z = 620 (M-H)".
With triethylamine; In dichloromethane; at -78 - 20℃; for 1h; 2.3 g of naphthyl dichlorophosphate and 2.2 g of <strong>[5557-81-3]L-alanine benzyl ester hydrochloride</strong> were dissolved in 30 mL of anhydrous dichloromethane and cooled to -78 C. A solution of 2 ml of triethylamine dissolved in 20 mL of anhydrous dichloromethane was added dropwise with stirring, and the dropping rate was controlled to maintain the reaction temperature at -78 C. After the addition was completed, the reaction temperature was slowly raised to room temperature, and stirring was continued for 1 hour. The solvent was evaporated under reduced pressure. The filtrate was evaporated to dryness under reduced pressure to give Intermediate ii-2, which was used directly for the next step.

  • 20
  • [ 5557-81-3 ]
  • [ 19430-76-3 ]
  • C16H16BrClNO4P [ No CAS ]
  • 21
  • [ 5557-81-3 ]
  • [ 15074-54-1 ]
  • C16H16Cl2NO4P [ No CAS ]
  • 22
  • [ 22329-38-0 ]
  • [ 5557-81-3 ]
  • 2-[(1-methyl-9<i>H</i>-β-carboline-3-carbonyl)-amino]-propionic acid benzyl ester [ No CAS ]
  • 23
  • [ 75-44-5 ]
  • [ 5557-81-3 ]
  • C11H12ClNO3 [ No CAS ]
  • 24
  • [ 31651-74-8 ]
  • [ 5557-81-3 ]
  • C10H7OPOClNHCH(CH3)COOC7H7 [ No CAS ]
  • 25
  • [ 5557-81-3 ]
  • (2R,3R)-2-tert-Butoxycarbonylamino-3-phenyl-pent-4-enoic acid [ No CAS ]
  • benzyl (S)-2-[(2R,3R)-2-(tert-butyloxycarbonyl)amino-3-phenylpent-4-enoylamino]propanoate [ No CAS ]
  • 26
  • [ 13139-15-6 ]
  • [ 5557-81-3 ]
  • [ 66415-01-8 ]
  • 28
  • [ 100-39-0 ]
  • (1R,2R)-O-Merrifield bound N-(2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-2'-phenylacetamide [ No CAS ]
  • [ 5557-81-3 ]
  • 29
  • [ 5557-81-3 ]
  • (S)-benzyl 2-((((2S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methoxy)(naphthalen-1-yloxy)phosphorylamino)propanoate [ No CAS ]
  • 30
  • [ 5557-81-3 ]
  • (S)-benzyl 2-((((2S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-2-yl)methoxy)(naphthalen-1-yloxy)phosphorylamino)propanoate [ No CAS ]
  • 31
  • [ 5557-81-3 ]
  • [ 766513-85-3 ]
  • 32
  • [ 5557-81-3 ]
  • [ 766513-86-4 ]
  • 33
  • [ 5557-81-3 ]
  • C28H45N3O7*ClH [ No CAS ]
  • 34
  • [ 5557-81-3 ]
  • [ 766513-88-6 ]
  • 35
  • [ 5557-81-3 ]
  • N-(L-leucyl)-L-alanine benzyl ester hydrochloride [ No CAS ]
  • 36
  • [ 5557-81-3 ]
  • [ 714251-86-2 ]
  • 37
  • [ 5557-81-3 ]
  • (S)-2-[(2R,4R)-4-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-[1,3]dioxolan-2-ylmethoxy]-phenoxy-phosphorylamino}-propionic acid benzyl ester [ No CAS ]
  • 38
  • [ 5557-81-3 ]
  • (S)-2-{(4-Bromo-phenoxy)-[(2R,4R)-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-[1,3]dioxolan-2-ylmethoxy]-phosphorylamino}-propionic acid benzyl ester [ No CAS ]
  • 39
  • [ 5557-81-3 ]
  • (S)-2-{(2-Chloro-phenoxy)-[(2R,4R)-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-[1,3]dioxolan-2-ylmethoxy]-phosphorylamino}-propionic acid benzyl ester [ No CAS ]
  • 40
  • [ 5557-81-3 ]
  • (S)-2-[[(2R,4R)-4-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-[1,3]dioxolan-2-ylmethoxy]-(naphthalen-1-yloxy)-phosphorylamino]-propionic acid benzyl ester [ No CAS ]
  • 41
  • [ 5557-81-3 ]
  • (E)-5-(2-bromovinyl)-2’-deoxyuridine-5’-(1-phenylbenzyloxy-L-alaninyl)phosphate [ No CAS ]
  • 42
  • [ 5557-81-3 ]
  • (E)-5-(2-bromovinyl)-2'-deoxyuridine-5'-[para-nitrophenyl-(benzoxy-L-alaninyl)]-phosphate [ No CAS ]
  • 43
  • [ 5557-81-3 ]
  • [ 613244-82-9 ]
  • 44
  • [ 5557-81-3 ]
  • [ 613244-61-4 ]
  • 45
  • [ 5557-81-3 ]
  • [ 613244-60-3 ]
  • 46
  • [ 5557-81-3 ]
  • [ 676602-53-2 ]
  • 47
  • [ 5557-81-3 ]
  • N-(9-fluorenylmethoxycarbonyl)-S-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-cysteine-L-alanine benzyl ester [ No CAS ]
  • 48
  • [ 5557-81-3 ]
  • (S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-4,4,4-trifluoro-butyrylamino]-propionic acid benzyl ester [ No CAS ]
  • 49
  • [ 5557-81-3 ]
  • (S)-2-((S)-2-Amino-4,4,4-trifluoro-butyrylamino)-propionic acid benzyl ester; hydrochloride [ No CAS ]
  • 50
  • [ 5557-81-3 ]
  • (S)-2-[(S)-2-((S)-2-Amino-propionylamino)-4,4,4-trifluoro-butyrylamino]-propionic acid benzyl ester; hydrochloride [ No CAS ]
  • 51
  • [ 5557-81-3 ]
  • (S)-2-((S)-2-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexanoylamino]-propionylamino}-4,4,4-trifluoro-butyrylamino)-propionic acid benzyl ester [ No CAS ]
  • 52
  • [ 5557-81-3 ]
  • (S)-2-((S)-2-{(S)-2-[(S)-2-Amino-6-(2-chloro-benzyloxycarbonylamino)-hexanoylamino]-propionylamino}-4,4,4-trifluoro-butyrylamino)-propionic acid benzyl ester; compound with trifluoro-acetic acid [ No CAS ]
  • 53
  • [ 5557-81-3 ]
  • [ 266325-41-1 ]
  • 54
  • [ 5557-81-3 ]
  • H-Glu(OcHex)-Tfeg-Tfeg-Lys(ClZ)-Ala-Tfeg-Ala-OBzl*TFA [ No CAS ]
  • 55
  • [ 5557-81-3 ]
  • [ 69604-83-7 ]
  • 56
  • [ 5557-81-3 ]
  • [ 205175-09-3 ]
  • 57
  • [ 5557-81-3 ]
  • [ 181213-20-7 ]
  • 58
  • [ 5557-81-3 ]
  • [ 1026650-14-5 ]
  • 59
  • [ 5557-81-3 ]
  • Benzoic acid (S)-2-amino-2-((S)-1-benzyloxycarbonyl-ethylcarbamoyl)-propyl ester [ No CAS ]
  • 60
  • [ 5557-81-3 ]
  • Benzoic acid (S)-2-((S)-1-benzyloxycarbonyl-ethylcarbamoyl)-2-((S)-2-tert-butoxycarbonylamino-propionylamino)-propyl ester [ No CAS ]
  • 61
  • [ 5557-81-3 ]
  • Benzoic acid (R)-2-((S)-1-benzyloxycarbonyl-ethylcarbamoyl)-2-((S)-2-tert-butoxycarbonylamino-propionylamino)-propyl ester [ No CAS ]
  • 62
  • [ 5557-81-3 ]
  • Benzoic acid (S)-2-benzyl-3-((S)-1-benzyloxycarbonyl-ethylamino)-2-((S)-2-tert-butoxycarbonylamino-propionylamino)-but-3-enyl ester [ No CAS ]
  • 63
  • [ 5557-81-3 ]
  • H-Thr(Bzl)-AlA-OBzl hydrochloride [ No CAS ]
  • 64
  • [ 5557-81-3 ]
  • [ 126496-71-7 ]
  • 65
  • [ 5557-81-3 ]
  • (S)-2-((2S,3R)-2-{(S)-2-Amino-3-[4-(dimethoxy-phosphoryloxy)-phenyl]-propionylamino}-3-benzyloxy-butyrylamino)-propionic acid benzyl ester; hydrochloride [ No CAS ]
  • 66
  • [ 5557-81-3 ]
  • [ 126496-73-9 ]
  • 67
  • [ 5557-81-3 ]
  • (S)-4-Amino-4-{(S)-1-[(1S,2R)-2-benzyloxy-1-((S)-1-benzyloxycarbonyl-ethylcarbamoyl)-propylcarbamoyl]-2-[4-(dimethoxy-phosphoryloxy)-phenyl]-ethylcarbamoyl}-butyric acid benzyl ester; hydrochloride [ No CAS ]
  • 68
  • [ 5557-81-3 ]
  • [ 126496-75-1 ]
  • 69
  • [ 5557-81-3 ]
  • [ 63983-90-4 ]
  • 72
  • [ 5557-81-3 ]
  • (S)-2-[(S)-2-((S)-2-Amino-6-benzyloxycarbonylamino-hexanoylamino)-3-benzyloxy-propionylamino]-propionic acid benzyl ester [ No CAS ]
  • 74
  • [ 5557-81-3 ]
  • (S)-2-{(S)-2-[(S)-2-((S)-2-Amino-propionylamino)-6-benzyloxycarbonylamino-hexanoylamino]-3-benzyloxy-propionylamino}-propionic acid benzyl ester [ No CAS ]
  • 76
  • [ 5557-81-3 ]
  • (S)-2-[(S)-3-Benzyloxy-2-((S)-6-benzyloxycarbonylamino-2-{(S)-2-[((S)-pyrrolidine-2-carbonyl)-amino]-propionylamino}-hexanoylamino)-propionylamino]-propionic acid benzyl ester [ No CAS ]
  • 78
  • [ 5557-81-3 ]
  • (S)-2-{(S)-2-[(S)-2-((S)-2-[(S)-1-((S)-2-Amino-6-benzyloxycarbonylamino-hexanoyl)-pyrrolidine-2-carbonyl]-amino}-propionylamino)-6-benzyloxycarbonylamino-hexanoylamino]-3-benzyloxy-propionylamino}-propionic acid benzyl ester [ No CAS ]
  • 80
  • [ 5557-81-3 ]
  • C62H83N9O13 [ No CAS ]
  • 81
  • [ 5557-81-3 ]
  • [ 96467-84-4 ]
  • 82
  • [ 5557-81-3 ]
  • <i>N</i>-(<i>N</i>2-benzyloxycarbonyl-<i>N</i>5-benzyloxycarbonylmethyl-L-glutaminyl)-L-alanine benzyl ester [ No CAS ]
  • 83
  • [ 5557-81-3 ]
  • <i>N</i>-[<i>N</i>2-benzyloxycarbonyl-<i>N</i>5-((<i>R</i>)-1-benzyloxycarbonyl-ethyl)-L-glutaminyl]-L-alanine benzyl ester [ No CAS ]
  • 84
  • [ 56-41-7 ]
  • [ 100-51-6 ]
  • [ 5557-81-3 ]
YieldReaction ConditionsOperation in experiment
58% EXAMPLE 43 The Preparation of HCl.Ala-OBzl To the solution of 25 ml of benzyl alcohol and 5 g of polyphosphoric acid 1070 mg (0.012 mmol) of L-Ala were added. The reaction mixture was stirred at 90-95.box. for 4 h and TLC (chloroform/methanol, 20:1) indicated complete disappearance of L-Ala. The reaction mixture was pured into the solution of 10 ml of concentrated hydrochloric acid in 200 ml of water. The formed solution was extracted with ether (50 ml*3) and separated. The organic phase was washed with hydrochloric acid(2percent, 30 ml*3). The combined water phases was adjusted to pH 10 with sodium carbonate. The water phase was extracted with 100 ml of ether and then dried over anhydrous Na2SO4. After filtration to the filtrate hydrogen chloride gas was introduced to precipitate the title compound. The precipitates were filtered and dry over anhydrous CaCl2 to provide 1500 mg (58percent) of the title compound as a crystal. Mp140-142° C.
  • 85
  • [ 15761-39-4 ]
  • [ 5557-81-3 ]
  • [ 52616-95-2 ]
YieldReaction ConditionsOperation in experiment
89% With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 - 20℃; for 8h;pH 9; At 0° C. the solution of 500 mg (2.326 mmol) of HCl Ala-OBzl in 5 ml of anhydrous tetrahydrofuran was adjusted to pH 9, to which the pre-cold solution of 500 mg (2.326 mmol) of Boc-Pro-OH, 300 mg (2.222 mmol) of 1-hydroxybenzotriazole and 480 mg (2.331 mmol) of dicyclohexylcarbodiimide in 30 ml of anhydrous tetrahydrofuran was added. The reaction mixture was stirred at 0° C. for 2 h and at room temperature for 6 h and TLC (chloroform/methanol, 30:1) indicated complete disappearance of HCl.Ala-Lys(ClZ)-OBzl. The resulted precipitates of N,N-dicyclohexylurea were filtrated and the filtrate was diluted with 80 ml of ethyl acetate. The solution obtained was washed successively with saturated NaCO3 in water (50 ml.x.3), saturated NaCl in water (50 ml.x.3) and KHSO4 in water (5percent, 30 ml.x.3). The separated ethyl acetate layer was dried with anhydrous MgSO4, and then evaporated to provide 782 mg (89percent) of the title compound as a colorless powder. Mp100-101° C., FAB-MS (m/e) 377[M+H]+.
75% With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20℃;Cooling with ice; In a round bottom flask, HCl.H-Ala-OBzl (5g, 23mmol) was dissolved in DMF and placed over ice bath. To this reaction mixture, triethylamine (4ml, 28mmol), Boc-Pro-OH (5.9g, 28mmol), HOBT.H2O (4.3g, 28mmol) and DCC (5.8g, 28mmol) was added and stirred at room temperature for overnight. Upon the completion of reaction as monitored by TLC, the solvent was evaporated, the residue was dissolved in ethyl acetate and 10percent citric acid solution was added to precipitate DCU. The DCU was filtered, the filtrate was washed with 10percent citric acid, brine , 4percent NaHCO3 and brine respectively for 3 times. Finally the organic layer was dried over MgSO4, filtered and dried yielding 75percent of titled compound with purity 100 percent as confirmed by HPLC. FTIR (KBr, cm-1): 3304-s (N-H stretch), 1736-s (C=O), 1250-s (C-O (carboxyl)), 1361-s (C-N aryl), 1210-s (C-N alkyl), 1544-s (N-H bend), 852-w (N-H (oop)), 740-s (C-H (oop)).
  • 86
  • [ 782493-67-8 ]
  • [ 5557-81-3 ]
  • C33H42F3N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; triethylamine; In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; at 20℃; for 168h; Step B: L-alanine benzylester hydrochloride (11mg, 0. 062MMOL), triethylamine (9. 0muL, 0.062mmol), and sodium triacetoxyborohydride (22mg, 0. 10MMOL) were added to a stirring solution of 1- ((1R,3S)-3-isopropyl-3-[6-(trifluoromethyl)-2H-1, 3-benzoxazin-3 (4H)- yl] CARBONYL} CYCLOPENTYL) PIPERIDIN-4-ONE (19MG, 0. 021mmol) in DCM (lOmL). The reaction mixture was stirred at rt for 96h, however, the reaction had not gone to completion. Another 19mg (0. 11mmol) of L- alanine benzylester hydrochloride and 15muL (0.11mmol) of triethylamine was added to the reaction mixture. After stirring for an additional 72h at rt, the reaction mixture was diluted with dichloromethane (50ML), washed with sodium bicarbonate solution (1 x 50ML) and brine (1 x 50ML), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by preparatory TLC (silica gel, 0.25percent ammonium hydroxide, 2.25percent MeOH, 97.5percent DCM) afforded the desired product. ESI- MS calculated for C33H42F3N304 : 601. 70, found 602 (M + H).
With sodium tris(acetoxy)borohydride; triethylamine; In dichloromethane; at 20℃; for 168h; Step B: L-alanine benzylester hydrochloride (11 mg, 0.062 mmol), triethylamine (9.0 muL, 0.062 mmol), and sodium triacetoxyborohydride (22 mg, 0.10 mmol) were added to a stirring solution of 1-((1R,3S)-3-isopropyl-3-([6-(trifluoromethyl)-2H-1,3-benzoxazin-3(4H)-yl]carbonylcyclopentyl)piperidin-4-one (19 mg, 0.021 mmol) in DCM (10 mL). The reaction mixture was stirred at rt for 96 h, however, the reaction had not gone to completion. Another 19 mg (0.11 mmol) of L-alanine benzylester hydrochloride and 15 muL (0.11 mmol) of triethylamine was added to the reaction mixture. After stirring for an additional 72 h at rt, the reaction mixture was diluted with dichloromethane (50 mL), washed with sodium bicarbonate solution (1.x.50 mL) and brine (1.x.50 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by preparatory TLC (silica gel, 0.25percent ammonium hydroxide, 2.25percent MeOH, 97.5percent DCM) afforded the desired product. ESI-MS calculated for C33H42F3N3O4: 601.70. found 602 (M+H).
  • 87
  • [ 20464-68-0 ]
  • [ 5557-81-3 ]
  • [ 860638-34-2 ]
YieldReaction ConditionsOperation in experiment
92% With triethylamine; In dichloromethane; at -78 - 20℃; for 1h; Preparation of 4-methoxyphenyl (benzoxy-L-alaninyl) phosphorochloridate:; 4-Methoxyphenyl phosphorodichloridate (6.6 g, 27.38 mmol) and L-alanine-benzyl ester hydrochloride salt (5.91 g, 27. 38 mmol) were suspended in 100 ml of anhydrous DCM. Anhydrous triethylamine (7.6 ml, 57.77 mmol). in 20 ml of dry DCM was added dropwise at-78 C under nitrogen. Following the addition, the reaction mixture was slowly allowed to warm at room temperature and stirred for one hour. The solvent was removed under reduced pressure and the solid obtained was washed with anhydrous ether (2 x 20 ml), filtered and the filtrate reduced to dryness to give the crude product (9.66 g, 92%) as an oil, which was used in the following step without any further purification. 31p nmr (Cl3, 121 MHz): 9.8, 9.5
  • 88
  • [ 105184-38-1 ]
  • [ 5557-81-3 ]
  • [ 649736-97-0 ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 20℃; for 18h; A solution of 1.72 g of 3,5-difluorophenyl-acetic acid in 50 ml of dimethylformamide at 0° C. is admixed with 1.01 g of N-methylmorpholine, 5.72 g of PyBOP, 2.15 g of <strong>[5557-81-3](S)-alanine benzyl ester hydrochloride</strong> and 1.01 g of N-methylmorpholine. The mixture is allowed to return to ambient temperature and is stirred for 18 h. The reaction medium is evaporated and the residue is taken up in ethyl acetate and washed twice with saturated aqueous sodium bicarbonate solution, a solution of potassium hydrogen sulfate (1M) and then with saturated aqueous sodium chloride solution. The organic phase is dried over anhydrous sodium sulfate. The residue is chromatographed on a silica gel column, eluding with a 7:3 (v/v) petroleum ether/ethyl acetate mixture, to give 1.9 g of a white solid. NMR 300 MHz (CDC13) delta ppm: 1.40 (d, 3H); 3.54 (s, 2H); 4.62 (m, 1H); 5.18 (m, 2H); 6.10 (d, 1H); 6.73 (t, 2H); 6.80 (d, 1H); 7.32 (m, 5H). A solution of 1.9 g of N-3,5-difluorophenylacetyl-(S)-alanine benzyl ester in 80 ml of absolute ethanol is admixed with 300 mg of 10percent palladium on carbon. The reaction medium is hydrogenated at atmospheric pressure and at ambient temperature for 8 h. The reaction medium is filtered on paper, washed with absolute ethanol and then evaporated. This gives 1.37 g of a white solid. NMR 300 MHz (CDC13) delta ppm: 1.36 (d, 3H); 3.48 (s, 2H); 3.70 (s, 1H); 4.40 (m, 1H); 6.65 (t, 2H); 6.70 (d, 1H); 6.95 (d, 1H).
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