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CAS No. : | 383-70-0 | MDL No. : | MFCD00029784 |
Formula : | C4H4F3NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IFAXXCBMQJNCCF-UHFFFAOYSA-N |
M.W : | 171.07 | Pubchem ID : | 136227 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 26.31 |
TPSA : | 66.4 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.17 cm/s |
Log Po/w (iLOGP) : | 0.84 |
Log Po/w (XLOGP3) : | 0.25 |
Log Po/w (WLOGP) : | 1.01 |
Log Po/w (MLOGP) : | -0.35 |
Log Po/w (SILICOS-IT) : | 0.21 |
Consensus Log Po/w : | 0.39 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -0.79 |
Solubility : | 27.5 mg/ml ; 0.161 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.21 |
Solubility : | 10.7 mg/ml ; 0.0624 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.54 |
Solubility : | 49.3 mg/ml ; 0.288 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.29 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triethylamine In methanol at 20℃; for 24 h; | General procedure: The TFA-α-amino acid was prepared with reported procedure [1,2] with slightly modification.Triethylamine (33 mmol, 1.5 equiv.) was added to a solution of α-amino acid (22 mmol) inMeOH (22 mL). After 5 min, ethyl trifluoroacetate (29 mmol, 1.3 equiv.) was added and thereaction was allowed to stir for 24 h. The solvent was removed by rotary evaporation and theresidue that remained was dissolved in H2O (35 mL) and acidified with concentrated HCl (4 mL).After stirring for 15 min, the mixture was extracted with ethyl acetate and the organic layerswere combined and washed with brine, dried by MgSO4, filtered, and concentrated by rotaryevaporation. Further subjection into high vacuum for overnight, if needed to solidify the product(L-/D-1a–L-/D-2a, 3a, L-/D-4a–L-/D-8a). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | at 0 - 70℃; for 2 h; Large scale | To a 30 L reactor equipped with a mechanical stirrer, a thermometer,a reflux condenser, an addition funnel, and nitrogeninlet-outlet was charged TFA (2 L), glycine 16 (2.0 kg, 26.6 mol)with stirring while keeping the inner temperature below 0 Cresulting in a suspension. Then to the suspension was added dropwiseTFAA (6.6 kg, 31.4 mol) with stirring while keeping the innertemperature below 70 C. After addition, the reaction mixture waskept at 70 C and stirred for another 2 h until all solid was dissolved.Completion was demonstrated by disappearance of thestarting material by HPLC after 2 h. The mixture was concentratedto dryness under vacuum at 50 C to obtain the crude 17 as a lightyellow solid. The crude material was purified by re-crystallizationfrom EtOAc (6 L) and heptane (12 L) to afford pure 17 (3.7 kg, 81percent)as a white solid: mp 120–121 C. 1H NMR (400 MHz, D2O) d 4.01 (s,2 H). 13C NMR (101 MHz, D2O) d 40.86, 117.08, 159.37, 171.66;HRMS (ESI) [C4H4F3NO3H]) calcd 170.0065, found 170.0044. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With triethylamine In methanol for 18 h; | Methyl trifluoroacetate (804 μL, 7.99 mmoles) and triethylamine (928 μL, 6.66 mmoles) were added to a suspension of glycine (500 mg, 6.66 mmoles) in methanol (2.5 mL). After the mixture was stirred vigorously for 18 h, 1 N HCl was added dropwise until the a pH of 2 was obtained. The reaction was added to ethyl acetate (30 mL) was washed with 1 N HCl (2 x 10 mL), dried over MgSO4, and concentrated in vacuo to yield the amide as a white solid (991 mg, 5.79 mmoles, 87percent). LRMS: (CI+) calcd for C4H4NO3F3 (M + NH4): 189; found: 189. 1H NMR: spectrum is consistent with the predicted structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With triethylamine; In methanol; for 18h; | Methyl trifluoroacetate (804 muL, 7.99 mmoles) and triethylamine (928 muL, 6.66 mmoles) were added to a suspension of glycine (500 mg, 6.66 mmoles) in methanol (2.5 mL). After the mixture was stirred vigorously for 18 h, 1 N HCl was added dropwise until the a pH of 2 was obtained. The reaction was added to ethyl acetate (30 mL) was washed with 1 N HCl (2 x 10 mL), dried over MgSO4, and concentrated in vacuo to yield the amide as a white solid (991 mg, 5.79 mmoles, 87%). LRMS: (CI+) calcd for C4H4NO3F3 (M + NH4): 189; found: 189. 1H NMR: spectrum is consistent with the predicted structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 15 - 40℃; for 4h;Inert atmosphere; Large scale; | General procedure: To a 30 L reactor equipped with a mechanical stirrer, a thermometer,a reflux condenser, an addition funnel, and nitrogeninlet-outlet was charged CH2Cl2 (20 L), 17 (3.4 kg, 19.6 mol), DMF(0.01 L) with stirring to afford a clear solution. And then to thissolution was added dropwise oxalyl chloride (2.8 kg, 21.6 mol)for 30 min at 15 C under nitrogen protection. After addition, thereaction mixture was stirred at 40 C for 4 h. Completion wasdemonstrated by disappearance of the starting material by HPLCafter 4 h. The solvent was removed under vacuum at 40 C to afford2-(2,2,2-trifluoroacetamido) acetyl chloride (3.7 kg, 100%) as abrown oil which was directly used in the next step withoutpurification.To a stirred solution of crotyl alcohol (1.4 kg, 18.7 mol) in CH2-Cl2 (20 L) was added dropwise a solution of 2-(2,2,2-trifluoroacetamido)acetyl chloride (3.7 kg, 19.7 mol) in CH2Cl2 (1 L) at25 C over 30 min. After addition, the reaction mixture was stirredat 30 C overnight. At completion, the mixture was washed withH2O (3 5 L) and 5% NaHCO3 aqueous solution (3 5 L). The separatedorganic layer was dried over anhydrous Na2SO4 and evaporatedto dryness to obtain the crude product 18 which was purifiedby re-crystallization from CH2Cl2:THF:heptane (0.5 L:0.5 L:10 L) toobtain purified 18 (3.0 kg, 68%) as a white solid: mp 48-49 C; 1HNMR (400 MHz, CDCl3) 1.70 (br d, J = 6.36, 3H), 4.08 (br d, J = 5.26,2H), 4.58 (br d, J = 6.48, 2H), 5.45-5.65 (m, 1H), 5.72-5.90 (m, 1H),7.32 (br s, 1H); 13C NMR (101 MHz, CDCl3) 17.53, 41.21, 66.62,117.01, 123.91, 132.78, 157.57, 168.07; HRMS (ESI) [C8H10F3NO3-H] calcd 224.0535, found 224.0545. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With pyridine; In acetonitrile; at 20℃; for 3h; | Disuccinimidyl carbonate (300 mg, 1.17 mmoles) was added to a solution of 13 (200 mg, 1.17 mmoles) and pyridine (94.6 muL, 1.17 mmoles) in acetonitrile (1.0 mL). The reaction mixture was stirred at room temperature for 3 h, during which the solution became clear and evolved gas. The solution was added to ethyl acetate (10 mL), washed with 1N HCl (2 x 5 mL) and saturated aqueous NaHCO3 (2 x 5 mL), dried over MgSO4, and concentrated in vacuo to yield a white solid (232 mg, 865 mumoles, 74%). LRMS: (ES+) calcd for C8H7N2O5F3 (M + NH4): 286; found: 286. 1H NMR: spectrum is consistent with the predicted structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoroacetic anhydride; In ethyl acetate; trifluoroacetic acid; | N-Trifluoroacetylglycine A suspension of 100 g (1.33 mol) of glycine in 450 mL of TFA is treated with 385 mL (2.73 mol) of trifluoroacetic anhydride. The mixture is allowed to stir for 1.5 h. The mixture is concentrated in vacuo and is treated with 1 L of 1:1 chloroform-hexanes. The slurry is concentrated in vacuo, treated with 1 L of EtOAc, warmed, then allowed to cool to 25 C. and then to 4 C. The solid is collected and dried to afford 89.21 g of N-trifluoroacetylglycine as a solid. The filtrate is concentrated in vacuo, treated with EtOAc, warmed, and allowed to cool to 25 C. Collection of the solid affords a further 58.08 g of N-trifluoroacetylglycine. 1H NMR (400 MHz, CDCl3) delta 12.90 (s, 1H), 9.75 (s, 1H), 3.81 (s, 2H) ppm. | |
In tetrahydrofuran; chloroform; Petroleum ether; | Example 7 2-(2,2,2-Trifluoroacetamido)acetic acid (136) 23 ml (160.46 mmol, 2.0 eq) of TFA2O were added at 0 C. to a suspension of 6.023 g (80.23 mmol, 1.0 eq) of glycine 133 in 150 ml of THF and the mixture was subsequently stirred at room temperature for 3 h. The solvent was removed under reduced pressure, the residue was refluxed in 120 ml of CHCl3/petroleum ether 1:1 and the product 136 was filtered off as a white solid. The filtrate was concentrated again and taken up in 40 ml of CHCl3/petroleum ether 1:1, refluxed and further product 136 was filtered off as a white solid. 6.991 g (40.87 mmol, 51%) of the TFA-protected glycine 136 were obtained as a white powder. M (C4H4F3NO3): 171.07 g mol-1. Mp.: 123.8 C. 1H-NMR (300 MHz, CD3OD): delta (ppm)=4.01 (s, 2H, H2). 13C-NMR (75 MHz, CD3OD): delta (ppm)=41.69 (t, C2), 117.34 (q, J 286.1, C4), 159.47 (q, J 37.6, C3), 171.54 (s, C1). IR (ATR) 17 (cm-1)=3312 (s), 3102 (s), 2946 (m), 2570 (w), 2485 (w), 2438 (w), 1699 (s), 1557 (s), 1494 (m), 1407 (s), 1350 (s), 1154 (s, br), 1086 (s), 1014 (s), 964 (m), 942 (s), 845 (s), 772 (s), 730 (s), 681 (s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; | Example 3h (2E)-2-Buten-1-yl N-Trifluoroacetylglycinate A mixture of 143.1 g (836 mmol) of N-trifluoroacetylglycine in 1 L of DMF is chilled to -8 C. as 100 mL (844 mmol) of E-crotyl bromide is added dropwise, followed by addition of 140 mL (937 mmol) of DBU at -5 C. After 1.5 h at -5 C. and 2 h at -2 C. the mixture is allowed to warm to 25 C. The mixture is cooled to 0 C. and 40 mL more DBU is added. After warming to 25 C. the mixture is concentrated in vacuo. 1 L of 1:1 ether-water is added. The organic layer is separated, washed with water, 1 N HCl, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride. Drying and concentration in vacuo is followed by trituration of the oil with hexanes-EtOAC to provide a solid. Chromatography on silica gel (elution with 3:1 hexanes-EtOAc) affords 49.96 g of (2E)-2-buten-1-yl N-trifluoroacetylglycinate as an oil. 1H NMR (400 MHz, d6-DMSO) delta 9.87 (bs, 1H), 5.75 (m, 1H), 5.55 (m, 1H), 4.51 (d, 2H), 3.96 (d, 2H), 1.64 (d, 3H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | To a solution of glycine (2.5 g, 33.3 mmol, 1.0 eq) in MeOH triethylamine (4.6 ml, 33.3 mmol, 1.0 eq) was added dropwise. After stirring for 5 min ethyl trifluoroacetate (5.2 ml, 43.3 mmol, 1.3 eq) was added and the mixture was stirred for 16 h at room temperature during which time a clear solution formed. Then the reaction mixture was concentrated under reduced pressure and the resulting residue acidified with 2 N HCI before being extracted with EtOAc (3x75 ml). The organic layers were combined then washed with brine and dried over MgS04. The solvent was removed in vacuo to give the product (11 ) as a white crystalline solid (5.4 g, 31 .6 mmol, 95%).HRMS (ESI): m/z calc for C4H4F3N03[M-H]- 170.0060 found 170.0073DC (n-Hexan/EtOAc/n-Bu/H20/AcOH, 2:1 :1 :1 ): Rf = 0.6.1H-NMR (400 MHz, CDCI3): d (ppm) = 12.97 (br, 1 H), 9.85 (t, J= 6.0 Hz, 1 H), 3.92 (d, J= 6.0 Hz, 2 H)13C-NMR (100 MHz, CDCI3): d (ppm) = 169.96, 156.87, 1 17.61 , 41.08 | |
85% | With triethylamine; In methanol; at 20℃; for 24h; | General procedure: The TFA-alpha-amino acid was prepared with reported procedure [1,2] with slightly modification.Triethylamine (33 mmol, 1.5 equiv.) was added to a solution of alpha-amino acid (22 mmol) inMeOH (22 mL). After 5 min, ethyl trifluoroacetate (29 mmol, 1.3 equiv.) was added and thereaction was allowed to stir for 24 h. The solvent was removed by rotary evaporation and theresidue that remained was dissolved in H2O (35 mL) and acidified with concentrated HCl (4 mL).After stirring for 15 min, the mixture was extracted with ethyl acetate and the organic layerswere combined and washed with brine, dried by MgSO4, filtered, and concentrated by rotaryevaporation. Further subjection into high vacuum for overnight, if needed to solidify the product(L-/D-1a-L-/D-2a, 3a, L-/D-4a-L-/D-8a). |
With sodium methylate; In methanol; at 0 - 20℃; for 4h; | To a stirred suspension of 2 g (25.5 mmol) of glycine in 6 mL of a 30% w/w solution of sodium methoxide in methanol, 10 mL (51.10 mmol) of ethyl trifluoroacetate were slowly added at 0C. Then temperature was slowly increased to room temperature and the solution was stirred for 4 hours. Then methanol was evaporated and the residue was partitioned between aqueous HCI 1M and diethyl ether. The organic phase was extracted with diethyl ether (2x100 mL) and the combined organic layers were washed with brine (3x100 mL), dried over Na2S04 and the solvent was evaporated under reduced pressure. A white solid was obtained (3.61 g, 79%) and it was used with no further purification. NMR characterization : *H NMR (acetone-d6 400 MHz) d 8.90 (1H, bs, NH), 4.06 (2H, d, J = 5.86 Hz, CH2) 13C NMR (acetone-de, 100 M Hz) d 169.7 [C, COOH], 158.0 [C, q, 2JC-F=36.8 Hz, COCF3], 117.0 [C, q, Jc-F=285.3 Hz, COCF3] 41.4 [CH2] . 19F NMR (acetone-de 376 MHz) d -76.44 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | 14.5 ml (200 MMOL) Thionylchlorid werden bei 0 C INNERHALB von 1 Stunde zu einer Loesung von 34.2 g (200 MMOL) GLYCINTRIFLUORACETAT in 200 ml Dimethylacetamid getropft. Anschliessend gibt man bei 0 C 24.4 g (40 MMOL) 5- Amino-2,4, 6-triodisophthalsaeuredichlorid (EP 0033426, Sovak, 1/80 US) hinzu und ruehrt 4 Tage bei Raumtemp.. Man giesst die Reaktionsmischung in 5 Liter Eiswasser und filtert den AUSFALLENDEN Feststoff ab. Zur weiteren Aufreinigung wird der Filterrueckstand in 1000 ml Ethylacetat geloest, zweimal mit gesaettigter Natriumhydrogencarbonat-Loesung ausgeschuettelt, die organische Phase ueber Natriumsulfat getrocknet und das Loesungsmittel im Vakuum eingedampft. Ausbeute : 28.7 g (94 % d. Th. ) eines farblosen Feststoffes Elementaranalyse : ber. : C 20.47 H 0.79 N 3.67 GEF. : C 20.52 H 0.77 N 3.71 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | 14.5 mi (200 MMOL) THIONYLCHLORID werden bei 0 C INNERHALB von 1 Stunde zu einer Loesung von 34.2 g (200 MMOL) GLYCINTRIFLUORACETAT in 200 mi Dimethylacetamid getropft. Anschliessend gibt man bei 0 C 23.8 g (40 MMOL) 5- Amino-2,4, 6-triodisophthalsaeuredichlorid (DE 2943777, Schering AG, (Prioritaet : 26.10. 79)) hinzu und ruehrt 4 Tage bei Raumtemp.. Man giesst die Reaktionsmischung in 5 Liter Eiswasser und filtert den AUSFALLENDEN Feststoff ab. Zur weiteren Aufreinigung wird der Filterrueckstand in 1000 ml Ethylacetat geloest, zweimal mit gesaettigter Natriumhydrogencarbonat-Loesung ausgeschuettelt, die organische Phase ueber Natriumsulfat getrocknet und das Loesungsmittel im Vakuum eingedampft. Ausbeute : 29 3 g (97 % d. Th. ) eines farblosen Feststoffes Elementaranalyse : ber. : C 19.25 H 0.54 N 3. 74 gef. : C 19.39 H 0.57 N 3. 72 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃;Product distribution / selectivity; | A solution of 7 (50 mg, 0.13 mmol), EDCI (39 mg, 0.20 mmol), HOBT (27 mg, 0.20 mmol), F3CGlyOH (28 mg, 0.16 mmol) and triethylamine (54 mg, 0.54 mmol) in dichloromethane (3mL) was stirred at rt overnight. The reaction mixture was washed with water, dried and concentrated to give the crude product. The crude product was purified by chromatography to give the desired product (22 mg, 31%). |
31% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; | A solution of 7 (50 mg, 0.13 mmol), EDCI (39 mg, 0.20 mmol), HOBT (27 mg, 0.20 mmol), F3CGIyOH (28 mg, 0.16 mmol) and triethylamine (54 mg, 0.54 mmol) in dichloromethane (3mL) was stirred at rt overnight. The reaction mixture was washed with water, dried and concentrated to give the crude product. The crude product was purified by chromatography to give the desired product (22 mg, 31%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃;Product distribution / selectivity; | A solution of 7 (65 mg, 0.16 mmol), EDCI (46 mg, 0.24 mmol), HOBT (32 mg, 0.24 mmol), F3CGlyOH (42 mg, 0.24 mmol) and triethylamine (65 mg, 0.65 mmol) in dichloromethane (3 mL) was stirred at rt overnight. The reaction mixture was washed with water, dried and concentrated to give the crude product. The crude product was purified by chromatography to give the desired product (25 mg, 28%). |
28% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; | A solution of 7 (65 mg, 0.16 mmol), EDCI (46 mg, 0.24 mmol), HOBT (32 mg, 0.24 mmol), F3CGIyOH (42 mg, 0.24 mmol) and triethylamine (65 mg, 0.65 mmol) in dichloromethane (3 mL) was stirred at rt overnight. The reaction mixture was washed with water, dried and concentrated to give the crude product. The crude product was purified by chromatography to give the desired product (25 mg, 28%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃;Product distribution / selectivity; | A solution of 6 (crude) and trifluoroacetic acid (10 mL) indichloromethane (10 mL) stirred at rt for 2 hours. The reaction solution was concentrated to give the product (0.3 g).A solution of 7 (50 mg, 0.13 mmol), EDCI (44 mg, 0.23 mmol), HOBT (31 mg, 0.23 mmol), F3CGlyOH (39 mg, 0.23 mmol) and triethylamine (47 mg, 0.46 mmol) in dichloromethane (3 mL) was stirred at rt overnight. The reaction mixture was washed with water, dried and concentrated to give the crude product. The crude product was purified by chromatography to give the desired product (22 mg, 32%). |
32% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; | A solution of 7 (50 mg, 0.13 mmol), EDCI (44 mg, 0.23 mmol), HOBT (31 mg, 0.23 mmol), FsCGIyOH (39 mg, 0.23 mmol) and triethylamine (47 mg, 0.46 mmol) in dichloromethane (3 mL) was stirred at rt overnight. The reaction mixture was washed with water, dried and concentrated to give the crude product. The crude product was purified by chromatography to give the desired product (22 mg, 32%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 2h;Product distribution / selectivity; | 1 mmol of deacetylated compound of (44) or (45) or (46) and N- trifluoroacetyloamino acid (1 mmol) were dissolved at room temperature and dichloromethane (6 mL) was added with stirring. Dicyclohexylcarbodiimide (1 mmol) was added to the suspension and, after 2 h cooled to OC and filtrated. Each compound (47) or (48) or (49) was crystallized from dichloromethane: ethyl ether (1 :1) solution. The yield of (47), (48), and (49) was 64%, 67% and 75%, respectively. |
36% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; | A solution of 6 (50 mg, 0.13 mmol), EDCI (48 mg, 0.25 mmol), HOBT (34 mg, 0.25 mmol), F3CGIyOH (43 mg, 0.25 mmol) and triethylamine (63 mg, 0.63 mmol) in dichloromethane (3 mL) was stirred at rt overnight. The reaction mixture was washed with water, dried and concentrated to give the crude product. The crude product was purified by chromatography to give the desired product (25 mg, 36%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 2h;Product distribution / selectivity; | 1 mmol of deacetylated compound of (44) or (45) or (46) and N- trifluoroacetyloamino acid (1 mmol) were dissolved at room temperature and dichloromethane (6 mL) was added with stirring. Dicyclohexylcarbodiimide (1 mmol) was added to the suspension and, after 2 h cooled to OC and filtrated. Each compound (47) or (48) or (49) was crystallized from dichloromethane: ethyl ether (1 :1) solution. The yield of (47), (48), and (49) was 64%, 67% and 75%, respectively. |
36% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; | A solution of 6 (50 mg, 0.13 mmol), EDCI (49 mg, 0.26 mmol), HOBT (35 mg, 0.26 mmol), F3CGIyOH (44 mg, 0.26 mmol) and triethylamine (65 mg, 0.65 mmol) in dichloromethane (3 mL) was stirred at rt overnight. The reaction mixture was washed with water, dried and concentrated to give the crude product. The crude product was purified by chromatography to give the desired product (25 mg, 36%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 2h;Product distribution / selectivity; | 1 mmol of deacetylated compound of (44) or (45) or (46) and N- trifluoroacetyloamino acid (1 mmol) were dissolved at room temperature and dichloromethane (6 mL) was added with stirring. Dicyclohexylcarbodiimide (1 mmol) was added to the suspension and, after 2 h cooled to OC and filtrated. Each compound (47) or (48) or (49) was crystallized from dichloromethane: ethyl ether (1 :1) solution. The yield of (47), (48), and (49) was 64%, 67% and 75%, respectively. |
64% | With dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 2h; | General procedure: 1 mmol of deacetylated compound of (44) or (45) or (46) and N- trifluoroacetyloamino acid (1 mmol) were dissolved at room temperature and dichloromethane (6 mL) was added with stirring. Dicyclohexylcarbodiimide (1 mmol) was added to the suspension and, after 2 h cooled to 0C and filtrated. Each compound (47) or (48) or (49) was crystallized from dichloromethane: ethyl ether (1 :1) solution. The yield of (47), (48), and (49) was 64%, 67% and 75%, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With dmap; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Product distribution / selectivity; | A solution of 4 (200 mg, 0.56 mmol), DCC (138 mg, 0.67 mmol), DMAP (82 mg, 0.67 mmol), and triethylamine (115 mg, 1.12 mmol) indichloromethane (5 ml_) was stirred at rt overnight. The reaction mixture was washed with water and concentrated to give the crude product. The crude product was purified by silica gel column chromatography to give they desired product (110 mg, 39%). |
39% | With dmap; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; | A solution of 4 (200 mg, 0.56 mmol), DCC (138 mg, 0.67 mmol), DMAP (82 mg, 0.67 mmol), and triethylamine (1 15 mg, 1.12 mmol) in dichloromethane (5 mL) was stirred at rt overnight. The reaction mixture was washed with water and concentrated to give the crude product. The crude product was purified by silica gel column chromatography to give they desired product (1 10 mg, 39%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; | A solution of 6 (30 mg, 0.06 mmol), EDCI (24 mg, 0.13 mmol), HOBT(17 mg, 0.13 mmol), F3CGlyOH (22 mg, 0.13 mmol) and triethylamine (26 mg,0.26 mmol) in dichloromethane (3 ml_) was stirred at rt overnight. The reaction mixture was washed with water, dried and concentrated to give the crude product which was directly used for the next step without further purification. | |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; | A solution of 6 (30 mg, 0.06 mmol), EDCI (24 mg, 0.13 mmol), HOBT (17 mg, 0.13 mmol), F3CGIyOH (22 mg, 0.13 mmol) and triethylamine (26 mg, 0.26 mmol) in dichloromethane (3 mL) was stirred at rt overnight. The reaction mixture was washed with water, dried and concentrated to give the crude product which was directly used for the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 26: Synthesis of (Trifluoroacetyl-Glycyl)2- Lysine2 mmol trifluoroacetyl glycine oil was dissolved in 2 mL DMF and 2 mL water. Added to this was 0.5 mmol lysine, followed by 2 mmol NMM, 2 mmol HOBt in 2 mL DMF, and 2 mmol PyBOP in 2 mL DMF, and allowed to react for 1 hour at room temperature. After one hour, the reaction was acidified with 1 mL 10% Tfa and 3 mL water. The reaction was then lyophilized overnight. Following lyopholization, 10 mL 10% Tfa was added, the solution filtered, and the filtrate frozen, thawed, re-filtered, and purified by C 18 chromatography. Removal of solvent afforded an orange oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Example 535 3-{2-(2,2,2-Trifluoroacetylamino)acetyl}-l-propynyl)-5'-C>-(4,4'-dimethoxytrityl] LNA uridineA solution of 2-(2,2,2-trifluoroacetamido)acetic acid (90 mg, 0.58 mmol), 0-(N-Succinimidyl)-l,l,3,3-tetramethyluronium tetrafluoroborate (TSTU, 190 mg, 0.63 mmol) and DIPEA (0.25 mL, 1.47 mmol) in DMF (10 mL) was stirred at room temperature for 30 minutes whereupon C5-propargylamine-5'-ODMTr LNA U (0.30 g, 0.49 mmol) was added to it. The reaction mixture stirred for 2h at rt. Whereupon solvents were removed at reduced pressure and the residue was taken in EtOAc (50mL) and washed with NaHC03 (2 x 50mL) followed by brine (50 mL). The organic phase was dried over Na2S04 and evaporated to dryness to afford crude which was purified by column chromatography (0-5 %MEOH/DCM) to afford desired nucleoside (180 mg, 48%) as slight brown solid material. Rt = 0.4 (5% MeOH in CH2C12, v/v); ¾ NMR (DMSO- ) (5 11.68 (s, 1H, ex, NH), 9.61 (t, 1H, ex, 7 = 5.5 Hz, NHCO), 8.49 (t, 1H, ex, 7 = 5.0 Hz, NHCO), 7.77 (s, 1H, H6), 7.42-7.44 (m, 2H, Ar), 7.28-7.34 (m, 6H, Ar), 7.24-7.26 (m, 1H, Ar), 6.91 (dd, 4H, 7 = 9.0 Hz, 2.5 Hz, Ar), 5.72 (d, 1H, ex, 7 = 5.0 Hz, 3'-OH), 5.42 (s, 1H, HI'), 4.24 (s, 1H, H2 , 4.03 (d, 1H, 7 = 5.0 Hz, H3'), 3.86-3.98 (m, 2H, CH2), 3.80-3.82 (m, 4H, CH2, 2 x H5"), 3.74 (s, 6H, 2 x OCH3), 3.55-3.57 (d, 1H, 7 = 11.0 Hz, H5'), 3.26-3.29 (d, 1H, 7 = 11.0 Hz, H5'); 13C NMR (DMSO- ) delta 166.6, 161.8, 158.1, 158.0, 156.6, 148.9, 144.6, 141.8, 135.4, 134.9, 129.7, 129.5, 127.8, 127.5, 126.6, 115.0, 113.25, 113.23, 97.5, 88.8, 87.5, 86.9, 85.5, 78.7, 74.7, 71.3, 69.6, 59.0, 54.9, 41.6, 28.7. |
[ 10009-20-8 ]
(S)-2-Amino-6-(2,2,2-trifluoroacetamido)hexanoic acid
Similarity: 0.70
[ 120097-65-6 ]
2-Acetamido-4,4,4-trifluorobutanoic acid
Similarity: 0.62
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H261 | In contact with water releases flammable gas |
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H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
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H314 | Causes severe skin burns and eye damage |
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H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
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H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
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H351 | Suspected of causing cancer |
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H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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