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[ CAS No. 5824-40-8 ] {[proInfo.proName]}

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Chemical Structure| 5824-40-8
Chemical Structure| 5824-40-8
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Product Details of [ 5824-40-8 ]

CAS No. :5824-40-8 MDL No. :MFCD00008047
Formula : C19H17N Boiling Point : -
Linear Structure Formula :- InChI Key :BZVJOYBTLHNRDW-UHFFFAOYSA-N
M.W : 259.35 Pubchem ID :138598
Synonyms :

Calculated chemistry of [ 5824-40-8 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.05
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 82.97
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.81
Log Po/w (XLOGP3) : 3.72
Log Po/w (WLOGP) : 3.83
Log Po/w (MLOGP) : 4.33
Log Po/w (SILICOS-IT) : 4.17
Consensus Log Po/w : 3.77

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.26
Solubility : 0.0143 mg/ml ; 0.000055 mol/l
Class : Moderately soluble
Log S (Ali) : -3.96
Solubility : 0.0286 mg/ml ; 0.00011 mol/l
Class : Soluble
Log S (SILICOS-IT) : -7.12
Solubility : 0.0000195 mg/ml ; 0.0000000752 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.89

Safety of [ 5824-40-8 ]

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 [ 5824-40-8 ]

* 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 [ 5824-40-8 ]

[ 5824-40-8 ] Synthesis Path-Downstream   1~85

  • 3
  • [ 696-59-3 ]
  • [ 5824-40-8 ]
  • [ 85684-89-5 ]
YieldReaction ConditionsOperation in experiment
87% With bismuth (III) nitrate pentahydrate; at 20℃; for 0.5h;Sonication; Neat (no solvent); General procedure: Amine 2 (1.0 mmol), 2,5-dimethoxytetrahydrofuran (1, 1.2 mmol) and bismuth nitrate pentahydrate (24 mg, 5 molpercent) was irradiated in a B5510-DTH (Branson ultrasonic cleaner; Model-5510, frequency 42 kHz with an output power 135 Watts), as specified in Table 2. After completion of the reaction (monitored by TLC) diethyl ether (10 mL) was added to the reaction mixture and filtered. Pure product was isolated from the reaction mixture after evaporation of ether.
  • 4
  • [ 25714-71-0 ]
  • [ 5824-40-8 ]
  • 4-[(E)-Tritylimino]-butan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium sulfate In ethanol for 12h;
  • 5
  • [ 14309-25-2 ]
  • [ 5824-40-8 ]
YieldReaction ConditionsOperation in experiment
95% With 1,3-diadamantane-4,5-dihydroimidazole chloride; potassium tert-butylate; bis(pinacol)diborane; copper(l) chloride; In toluene; at 25℃; for 4h;Schlenk technique; Inert atmosphere; General procedure: To a 10 mL Schlenk tube, B2pin2 (2.0 mmol, 2.0 equiv) was added to a toluene (2.0 mL) solution of CuCl (0.1 mmol, 10 mol%), IAmd·HCl (0.1 mmol, 10 mol%) andKOtBu (1.0 mmol, 1.0 equiv) at 25 C under argon atmosphere. The reaction mixturewas stirred at 25 C for 30 min. Then azide (1.0 mmol, 1.0 equiv) was added andevolution of gas was observed immediately. The resulting mixture was stirred for acertain time at 25 C until disappearance of the starting azide monitored by TLC. Thereaction was quenched by adding 25 mL H2O and 1M HCl aqueous solution to adjustPH = 4, and then the aqueous phase was basified to PH = 8 with Na2CO3. Theaqueous phase was extracted with ethyl acetate (30 mL×2). The organic phase wascombined and dried with Na2SO4 and evaporated to dryness to afford the amine whichwas in a few cases finally purified by silica column chromatography (DCM/MeOH).Analogous results were obtained by dissolving the azide into the toluene solution ofCuCl, IAmd·HCl and KOtBu, followed by adding B2pin2.
  • 6
  • [ 5824-40-8 ]
  • [ 105-39-5 ]
  • [ 18514-46-0 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In N,N-dimethyl-formamide 1.) 30 min, 50 deg C, 2.) 7 h room temp.;
  • 7
  • [ 5824-40-8 ]
  • [ 920-46-7 ]
  • N-triphenylmethylmethacrylamide [ No CAS ]
  • 9
  • [ 24767-82-6 ]
  • [ 5824-40-8 ]
  • [ 7370-54-9 ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine In toluene for 10h; Heating;
  • 10
  • [ 778-28-9 ]
  • [ 5824-40-8 ]
  • [ 7370-51-6 ]
  • 11
  • [ 5824-40-8 ]
  • [ 10157-76-3 ]
  • [ 848129-47-5 ]
  • 12
  • [ 5824-40-8 ]
  • [ 75-03-6 ]
  • [ 7370-34-5 ]
YieldReaction ConditionsOperation in experiment
28% In acetonitrile; Production Example 30 Synthesis of N-(triphenylmethyl)-N-ethylamine (Compound 30) <strong>[5824-40-8]Triphenylmethylamin</strong>e (1.00 g, 3.86 mmol) (Wako Pure Chemical Industries, Ltd.) and iodoethane (1.50 g, 9.62 mmol) (Wako Pure Chemical Industries, Ltd.) were dissolved in acetonitrile (5 mL) (Wako Pure Chemical Industries, Ltd.), and the mixture was left to stand still at room temperature for 3 days. The solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (chloroform (Wako Pure Chemical Industries, Ltd.) as an eluent), to thereby obtain the title compound (0.31 g, 28% yield). m.p. 75-77 C. 1H-NMR (CDCl3): delta1.06 (t, J=6.9 Hz, 3H), 1.98 (t, J=6.9 Hz, 2H), 7.13-7.45 (m, 15H).
28% In acetonitrile; at 20℃; for 72h; Production Example 30 Synthesis of N-(triphenylmethyl)-N-ethylamine (Compound 30) <strong>[5824-40-8]Triphenylmethylamin</strong>e (1.00 g, 3.86 mmol) (Wako Pure Chemical Industries, Ltd.) and iodoethane (1.50 g, 9.62 mmol) (Wako Pure Chemical Industries, Ltd.) were dissolved in acetonitrile (5 mL) (Wako Pure Chemical Industries, Ltd.), and the mixture was left to stand still at room temperature for 3 days. The solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (chloroform (Wako Pure Chemical Industries, Ltd.) as an eluent), to thereby obtain the title compound (0.31 g, 28% yield). m.p. 75-77 C. 1H-NMR (CDCl3): delta1.06 (t, J=6.9 Hz, 3H), 1.98 (t, J=6.9 Hz, 2H), 7.13-7.45 (m, 15H).
  • 13
  • [ 5824-40-8 ]
  • [ 210096-14-3 ]
  • N-trityl 3-(9-anthracenyl)-2-hydroxybenzaldimine [ No CAS ]
  • 14
  • [ 50-00-0 ]
  • [ 17176-77-1 ]
  • [ 5824-40-8 ]
  • [ 944471-83-4 ]
YieldReaction ConditionsOperation in experiment
95% General procedure: N-N-Bromosuccinimide (178mg, 1mmol) was added on a solution of corresponding ((tritylamino)methyl)phosphonate (1mmol) in CCl4 (3mL) The mixture was stirred in quartz flask under UV light until observing the disappearance of starting aminomethylphosphonate by 31P NMR. Then, the corresponding indole (2mmol) and phosphoric acid catalyst (0.1mmol) in CH2Cl2 (10mL) were added at room temperature and the reaction mixture was stirred for 36hat room temperature. After that, 20mL of water were added and the organic phase was extracted with CH2Cl2 (2×10mL) and dried of in MgSO4. The volatiles were distilled off at reduced pressure to yield the crude product, which was purified by column chromatography (AcOEt/Hexanes).Bromosuccinimide (178mg, 1mmol) was added on a solution of corresponding ((tritylamino)methyl)phosphonate (1mmol) in CCl4 (3mL) The mixture was stirred in quartz flask under UV light until observing the disappearance of starting aminomethylphosphonate by 31P NMR. Then, the corresponding indole (2mmol) and phosphoric acid catalyst (0.1mmol) in CH2Cl2 (10mL) were added at room temperature and the reaction mixture was stirred for 36hat room temperature. After that, 20mL of water were added and the organic phase was extracted with CH2Cl2 (2×10mL) and dried of in MgSO4. The volatiles were distilled off at reduced pressure to yield the crude product, which was purified by column chromatography (AcOEt/Hexanes).
92% Step 1 : dibenzyl ((tritylamino) Paraformaldehyde (1 .259 g, 41.9 mmol) and AcOH (0.437 mL, 7.63 mmol) were added to a mixture of triphenylmethanamine (9.99 g, 38.5 mmol) in Toluene (201 mL). The reaction was heated to 80 °C for 1 h. Dibenzyl phosphonate (8.42 mL, 38.1 mmol) was added, and the mixture was stirred at reflux for 3 h. The reaction was cooled to RT and stirred for 48 h. TEA (2.126 mL, 15.25 mmol) was added, and the mixture was concentrated. Purification by Si (0-50percent EtOAc/Hex) afforded the title compound as a colorless solid. (18.6 g, 92percent yield). MS (m/z) 534.1 (M+H)+
  • 15
  • [ 5824-40-8 ]
  • [ 89448-83-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 45 percent / 30 h / 120 °C 2: 80 percent / sodium hydride / dioxane / 1.) RT, 10 min, 2.) reflux, 48 h 3: 84 percent / perchloric acid, acetic acid / 1.) 0 deg C, 10 min, 2.) RT, 30 min, 3.) reflux, 60 h 4: 96 percent / thionyl chloride / heptane / 1.) RT, 10 min, 2.) reflux, 1 d 5: 83 percent / tetrahydrofuran / 1.) 0 deg C, 4 h, 2.) RT, 2 d
Multi-step reaction with 5 steps 1: 45 percent / 30 h / 120 °C 2: 80 percent / sodium hydride / dioxane / 1.) RT, 10 min, 2.) reflux, 48 h 3: 84 percent / methanol, perchloric acid, acetic acid / 1.) 0 deg C, 10 min, 2.) RT, 30 min, 3.) reflux, 60 h 4: 96 percent / thionyl chloride / heptane / 1.) RT, 10 min, 2.) reflux, 1 d 5: 83 percent / tetrahydrofuran / 1.) 0 deg C, 4 h, 2.) RT, 2 d
  • 16
  • [ 5824-40-8 ]
  • [ 13949-93-4 ]
  • ethyl 2-triphenylmethylaminomethylcyclopropane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium cyanoborohydride; magnesium sulfate; In methanol; hexane; ethyl acetate; Step A: Ethyl 2-triphenylmethylaminomethylcyclopropane-1-carboxylate To a mixture of ethyl 2-formylcyclopropane-1-carboxylate (1.00 g; 7.03 mmol) and magnesium sulfate (0.85 g; 7.03 mmol) in 50 ml methanol is added tritylamine (1.82 g; 7.03 mmol). To this is then added sodium cyanoborohydride (0.88 g; 14.06 mmol) and stirred for 48 hrs. To this is then further added 0.20 g of ethyl 2-formylcyclopropane-1-carboxylate and stirring continued for another 72 hrs. The reaction mixture is filtered, concentrated in vacuo and flash chromatographed using hexane:ethylacetate; 9:1 to obtain ethyl-2-triphenylmethylaminomethyl-cyclopropane-1-carboxylate as a colorless oil which is used directly in the next step.
  • 17
  • [ 5824-40-8 ]
  • [ 598-21-0 ]
  • [ 188112-22-3 ]
YieldReaction ConditionsOperation in experiment
In chloroform; PREPARATION 9 2-bromo-N-(triphenylmethyl) acetamide 3.22 ml of bromoacetyl bromide were added dropwise under an inert gas atmosphere at 0 C. to 19.23 g of tritylamine in 50 ml of chloroform and then the mixture was stirred for one hour while allowing the temperature to rise to ambient temperature. After filtration of the precipitate, the organic phase was washed with 1N sodium hydroxide, dried, evaporated under reduced pressure until a residue was obtained which was purified by crystallization from ether to obtain 8.5 g of the expected amide. NMR (CDCl3)
  • 18
  • [ 5824-40-8 ]
  • [ 17609-52-8 ]
  • [ 1120347-65-0 ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: Z-D-phenylglycine With 4-methyl-morpholine; methyl chloroformate In tetrahydrofuran at 0℃; for 1h; Stage #2: Triphenylmethylamin With 4-methyl-morpholine In tetrahydrofuran at 0 - 20℃; for 18h; Further stages.;
  • 19
  • [ 15975-93-6 ]
  • [ 5824-40-8 ]
  • [ 124685-71-8 ]
YieldReaction ConditionsOperation in experiment
In methanol; at 20 - 120℃; for 84.07h;Conversion of starting material; 62 mg (0.24 mmol) triphenylmethylamine (62 mg, 0.24 mmol) and 38 mg (0.13 mmol) <strong>[2420-87-3]3,3',4,4'-biphenyltetracarboxylic dianhydride</strong> were placed in a mortar and pestle. 20muL of methanol solvent was added and the mixture was ground for four minutes at room temperature. This white product was characterized by IR and PXRD and identified as a mixture. The powder was then transferred to an oven and was heated for 84 hours at 120 0C. The resulting light pink powder was characterized by IR and PXRD. See FIGS. 5A-5C.
  • 21
  • [ 5824-40-8 ]
  • [ 1466-88-2 ]
  • [ 1033942-45-8 ]
YieldReaction ConditionsOperation in experiment
In methanol at 20 - 100℃; for 12.07h; 24 Triphenylmethylamine (78 mg, 3 10"3 mol) and o-nitrocinnamaldehyde (53 mg, 3 10" mol) were placed in a mortar and pestle. 26μL of methanol was added and the mixture was ground for four minutes at room temperature. This white-yellow product was characterized by IR and PXRD. The powder was then transferred to an oven and was heated for 12 hours at 100 °C. The resulting white-yellow powder was characterized by IR and PXRD. See Figs. 25A and 25B where PA5 is triphenylmethylamine, AL5 is o-nitrocinnamaldehyde, OG43.37 is solvent drop grind and OG43.37 100 is product at 100°C.
  • 22
  • [ 89-93-0 ]
  • [ 2620-50-0 ]
  • [ 6068-70-8 ]
  • [ 5824-40-8 ]
  • [ 33166-49-3 ]
  • [ 51586-20-0 ]
  • [ 100-81-2 ]
  • [ 108-44-1 ]
  • [ 618-36-0 ]
  • [ 95-68-1 ]
  • [ 87-62-7 ]
  • [ 88-05-1 ]
  • [ 95-53-4 ]
  • [ 91-00-9 ]
  • 2,2,2-triphenyl-<i>N</i>-<i>m</i>-tolyl-acetamide [ No CAS ]
  • 2,2,2-triphenyl-<i>N</i>-(1-phenyl-ethyl)-acetamide [ No CAS ]
  • 2,2,2-triphenyl-<i>N</i>-<i>o</i>-tolyl-acetamide [ No CAS ]
  • <i>N</i>-(3-methyl-benzyl)-2,2,2-triphenyl-acetamide [ No CAS ]
  • 3,3,3-triphenyl-<i>N</i>-<i>o</i>-tolyl-propionamide [ No CAS ]
  • 3,3,3-triphenyl-<i>N</i>-<i>m</i>-tolyl-propionamide [ No CAS ]
  • <i>N</i>-(2-methyl-benzyl)-2,2,2-triphenyl-acetamide [ No CAS ]
  • 3,3,3-triphenyl-<i>N</i>-(1-phenyl-ethyl)-propionamide [ No CAS ]
  • <i>N</i>-(2,6-dimethyl-phenyl)-2,2,2-triphenyl-acetamide [ No CAS ]
  • <i>N</i>-(2,4-dimethyl-phenyl)-2,2,2-triphenyl-acetamide [ No CAS ]
  • <i>N</i>-(2,3-dimethyl-benzyl)-2,2,2-triphenyl-acetamide [ No CAS ]
  • <i>N</i>-(3-methyl-benzyl)-3,3,3-triphenyl-propionamide [ No CAS ]
  • <i>N</i>-(2,4-dimethyl-phenyl)-3,3,3-triphenyl-propionamide [ No CAS ]
  • <i>N</i>-(2-methyl-benzyl)-3,3,3-triphenyl-propionamide [ No CAS ]
  • <i>N</i>-benzhydryl-2,2,2-triphenyl-acetamide [ No CAS ]
  • <i>N</i>-(2,6-dimethyl-phenyl)-3,3,3-triphenyl-propionamide [ No CAS ]
  • 2,2,2-triphenyl-<i>N</i>-(2,4,6-trimethyl-phenyl)-acetamide [ No CAS ]
  • <i>N</i>-(2,3-dimethyl-benzyl)-3,3,3-triphenyl-propionamide [ No CAS ]
  • <i>N</i>-benzo[1,3]dioxol-5-ylmethyl-2,2,2-triphenyl-acetamide [ No CAS ]
  • 3,3,3-triphenyl-<i>N</i>-(2,4,6-trimethyl-phenyl)-propionamide [ No CAS ]
  • <i>N</i>-benzhydryl-3,3,3-triphenyl-propionamide [ No CAS ]
  • <i>N</i>-benzo[1,3]dioxol-5-ylmethyl-3,3,3-triphenyl-propionamide [ No CAS ]
  • C39H31NO [ No CAS ]
  • N-triphenylmethyl-3,3',3''-triphenylpropanamide [ No CAS ]
  • 23
  • [ 1107625-46-6 ]
  • [ 5824-40-8 ]
  • [ 1107625-47-7 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 60℃; for 2h; Part E:The dibromo compound 39 (192 mg, 0.52 mmol) was dissolved in DMF (5 ml_).DIEA (260 uL, 1.5 mmol) and tritylamine (148 mg, 0.57 mmol) was added and the mixture was heated to 60 °C and stirred for 2 hours. DMF was removed under vacuum and the residue was taken up with EtOAc (60 ml_). The organics was washed with water and brine and dried over Na2SO4. After concentration, the residue was purified with column (silica gel, 30percent EtOAc/Hexane) gave the product 40 (211 mg).
  • 24
  • [ 50-00-0 ]
  • [ 5824-40-8 ]
  • [ 538-60-3 ]
  • [ 944471-83-4 ]
YieldReaction ConditionsOperation in experiment
97% Example III; Dibenzyl [(thtyl-amino)-methvH-phosphonate; <n="42"/>A mixture of 1.00 g tritylamin in 20 ml of toluene is combined with 127 mg paraformaldehyde and 50 mul acetic acid and stirred for one hour at 800C. Then 0.85 ml dibenzylphosphite are added and the reaction mixture is refluxed for three hours. Then 200 mul triethylamine are added and the reaction mixture is evaporated down in vacuo using the rotary evaporator. The flask residue is chromatographed through a silica gel column. Yield: 2.0O g (97 percent of theory) Mass spectrum (ESI+): m/z = 534 [M+H]+
  • 27
  • C58H50N6O11S [ No CAS ]
  • [ 5824-40-8 ]
  • C48H42N4O7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% Example 79 To a solution of alcohol 99 (180 mg, 0.311 mmol) in anhydrous CH2Cl2 (8.0 mL) cooled to 0° C. was added 2,6-lutidine (90.0 muL, 0.777 mmol) followed by trifluoromethanesulfonic anhydride (TFAA) (62 muL, 0.373 mmol). After stirring for 30 min at 0° C., tritylamine (96 mg, 0.373 mmol) was added and the reaction was stirred for an additional 30 min at 0° C. The reaction mixture was subsequently diluted with CH2Cl2 (50 mL) and washed with saturated aqueous NaHCO3 (50 mL), water (50 mL) and brine (50 mL). The organic layer was dried over Na2SO4, concentrated and purified by column chromatography using 5percent EtOAc in CH2Cl2 as eluent to obtain 140 mg product (55percent yield).1H-NMR (400 MHz, CDCl3): 1.32 (s, 3H), 3.41 (s, 2H), 4.42 (d, 1H, J=12.07 Hz), 4.75 (d, 1H, J=12.07 Hz), 4.89 (s, 1H), 5.96 (s, 1H), 7.02 (s, 1H), 7.2-7.59 (m, 27H), 7.8 (s, 1H), 8.57 (d, 1H, J=5.32 Hz).
  • 28
  • [ 905273-63-4 ]
  • [ 5824-40-8 ]
  • [ 905273-65-6 ]
  • 30
  • [ 877218-24-1 ]
  • [ 5824-40-8 ]
  • C40H43NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% In acetonitrile; at 20℃; for 12h; Step a: 3,5-Dimethyl-4-(3-isopropyl-4-methoxymethoxybenzyl)benzyl bromide was prepared according to the procedure described for the synthesis of intermediate 4/step e. Trityl amine (530 mg, 2.04 mmol) was added to a solution of benzyl bromide (400 mg, 1.02 mmol) in acetonitrile (10 mL) at rt. After stirring at rt for 12 h, the solvent was removed under reduced pressure and the residue purified by column chromatography (4percent EtOAc in hexanes) to give the protected benzyl amine (320 mg, 55percent).
  • 31
  • [ 1622-32-8 ]
  • [ 5824-40-8 ]
  • [ 1207315-25-0 ]
YieldReaction ConditionsOperation in experiment
65% To 90 of a solution of 18.1 g (111 mmol) of 2-chloroethanesulfonylchloride in dichloromethane was charged dropwise 12.4 g (122 mmol) of triethylamine at -60°C, followed by stirring at the same temperature for 30 minutes and at room temperature for 1.5 hours. The reaction liquid was cooled to -60°C, and charged dropwise to 60 g of a solution of 28.8 g (111 mmol) of tritylamine and 11.2 g (111 mmol) of triethylamine in dichloromethane, followed by stirring at the same temperature for 1.5 hours, then stirring at room temperature for 4 hours, and leaving to stand overnight. Water was added to the reaction liquid, and the organic layer was washed with water, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was washed with ethyl acetate to prepare 25.2 g (yield 65percent) of a target compound. 1H-NMR (CDCl3, ppm) delta 5.21-5.23 (1H, m), 5.46-5.62 (3H, m), 7.22-7.33 (9H, m), 7.43-7.55 (6H, m).
  • 32
  • [ 97943-16-3 ]
  • [ 5824-40-8 ]
  • [ 1316009-08-1 ]
YieldReaction ConditionsOperation in experiment
General procedure: (a) To a solution of the 2-alkenoic acid (1 mmol) in dry dichloromethane (DCM, 3 mL), oxalyl chloride (COCl)2 (3.5 mmol, 0.3 mL) and two drops of DMF were added at 0 °C. The mixture was allowed to stir for 15 min at 0 °C and then for 2 h at rt, until no gas was observed. The solvent and the excess of oxalyl chloride were distilled off to dryness. The obtained acyl chloride was used in the next step without further purification.(b) The above obtained chloride was dissolved in dry DCM (5 mL) under argon and cooled at 0 °C. Et3N (5 mmol) was added, followed by addition of TrNH2 or other RNH2 (1 mmol) in DCM (3 mL) at 0 °C under stirring for 5 min. The resulting mixture was allowed to stir at rt until complete conversion, as indicated by TLC. The solvent was removed, the residue was redissolved in DCM, washed with water, an aqueous solution of 5percent potassium hydrogen sulfate (KHSO4) and brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by column chromatography on silica gel (methanol/dichloromethane, 1:20). The products, N-trityl-3-alkenamides, are white solids, mixtures of geometrical isomers E and Z, except of N-trityl-3-butenamide, as revealed from their 1H NMR spectra. Yield: 80-90percent.
  • 33
  • [ 100808-08-0 ]
  • [ 5824-40-8 ]
  • [ 1316009-22-9 ]
YieldReaction ConditionsOperation in experiment
General procedure: (a) To a solution of the 2-alkenoic acid (1 mmol) in dry dichloromethane (DCM, 3 mL), oxalyl chloride (COCl)2 (3.5 mmol, 0.3 mL) and two drops of DMF were added at 0 °C. The mixture was allowed to stir for 15 min at 0 °C and then for 2 h at rt, until no gas was observed. The solvent and the excess of oxalyl chloride were distilled off to dryness. The obtained acyl chloride was used in the next step without further purification.(b) The above obtained chloride was dissolved in dry DCM (5 mL) under argon and cooled at 0 °C. Et3N (5 mmol) was added, followed by addition of TrNH2 or other RNH2 (1 mmol) in DCM (3 mL) at 0 °C under stirring for 5 min. The resulting mixture was allowed to stir at rt until complete conversion, as indicated by TLC. The solvent was removed, the residue was redissolved in DCM, washed with water, an aqueous solution of 5percent potassium hydrogen sulfate (KHSO4) and brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by column chromatography on silica gel (methanol/dichloromethane, 1:20). The products, N-trityl-3-alkenamides, are white solids, mixtures of geometrical isomers E and Z, except of N-trityl-3-butenamide, as revealed from their 1H NMR spectra. Yield: 80-90percent.
  • 34
  • [ 625-35-4 ]
  • [ 5824-40-8 ]
  • [ 1316008-98-6 ]
YieldReaction ConditionsOperation in experiment
General procedure: (a) To a solution of the 2-alkenoic acid (1 mmol) in dry dichloromethane (DCM, 3 mL), oxalyl chloride (COCl)2 (3.5 mmol, 0.3 mL) and two drops of DMF were added at 0 °C. The mixture was allowed to stir for 15 min at 0 °C and then for 2 h at rt, until no gas was observed. The solvent and the excess of oxalyl chloride were distilled off to dryness. The obtained acyl chloride was used in the next step without further purification.(b) The above obtained chloride was dissolved in dry DCM (5 mL) under argon and cooled at 0 °C. Et3N (5 mmol) was added, followed by addition of TrNH2 or other RNH2 (1 mmol) in DCM (3 mL) at 0 °C under stirring for 5 min. The resulting mixture was allowed to stir at rt until complete conversion, as indicated by TLC. The solvent was removed, the residue was redissolved in DCM, washed with water, an aqueous solution of 5percent potassium hydrogen sulfate (KHSO4) and brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by column chromatography on silica gel (methanol/dichloromethane, 1:20). The products, N-trityl-3-alkenamides, are white solids, mixtures of geometrical isomers E and Z, except of N-trityl-3-butenamide, as revealed from their 1H NMR spectra. Yield: 80-90percent.
  • 35
  • [ 625-35-4 ]
  • [ 5824-40-8 ]
  • [ 132565-57-2 ]
YieldReaction ConditionsOperation in experiment
General procedure: (a) To a solution of the 2-alkenoic acid (1 mmol) in dry dichloromethane (DCM, 3 mL), oxalyl chloride (COCl)2 (3.5 mmol, 0.3 mL) and two drops of DMF were added at 0 °C. The mixture was allowed to stir for 15 min at 0 °C and then for 2 h at rt, until no gas was observed. The solvent and the excess of oxalyl chloride were distilled off to dryness. The obtained acyl chloride was used in the next step without further purification.(b) The above obtained chloride was dissolved in dry DCM (5 mL) under argon and cooled at 0 °C. Et3N (5 mmol) was added, followed by addition of TrNH2 or other RNH2 (1 mmol) in DCM (3 mL) at 0 °C under stirring for 5 min. The resulting mixture was allowed to stir at rt until complete conversion, as indicated by TLC. The solvent was removed, the residue was redissolved in DCM, washed with water, an aqueous solution of 5percent potassium hydrogen sulfate (KHSO4) and brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by column chromatography on silica gel (methanol/dichloromethane, 1:20). The products, N-trityl-3-alkenamides, are white solids, mixtures of geometrical isomers E and Z, except of N-trityl-3-butenamide, as revealed from their 1H NMR spectra. Yield: 80-90percent.
  • 36
  • [ 13419-69-7 ]
  • [ 5824-40-8 ]
  • N-trityl-3-hexenamide [ No CAS ]
  • N-trityl-2-hexenamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In dichloromethane at 0 - 20℃; 4.4. Typical procedure for the preparation of N-tritylamides from α,β-unsaturated acids with PyBroP as coupling reagent General procedure: To a solution of the carboxylic acid (1 mmol) in dry DCM (3 mL), TrNH2 (1 mmol), PyBroP (1 mmol) and Et3N (3 mmol) in DCM (2 mL) were added and the mixture was allowed to stir at 0 °C for 5 min and at rt overnight, until completion of the reaction. The mixture was then diluted with AcOEt (25 mL), washed with water, 5% KHSO4, dried over anhydrous Na2SO4, concentrated in vacuo and purified by column chromatography on silica gel. The obtained N-tritylamides were mixtures of α,β- and β,γ-unsaturated compounds, as identified by 1H NMR spectroscopy.
  • 37
  • [ 5824-40-8 ]
  • [ 1374138-04-1 ]
  • [ 1374138-05-2 ]
YieldReaction ConditionsOperation in experiment
Step 9: preparation of ben2yl [(25)-l-[1/2ri-butyl(diphenyl)silyl]oxy}-5-fluoro-6- (tritylamino)hexan-2-yl](3-methylbutyl)carbamate; To a stirred solution of the material from Step 8 (900 mg, 1.52 mmol) in dichloroethane (15 mL) at room temperature were added tritylamine (394 mg, 1.52 mmol) and sodium triacetoxyborohydride (483 mg, 2.28 mmol). The reaction mixture was stirred at room temperature overnight, poured into saturated aqueous NaHCC>3, ^ extracted with dichloromethane (2X). The combined organics were dried over MgSO.}, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silicaEtOAc-hexanes to yield 1.2 g of the title compound.
  • 38
  • [ 5824-40-8 ]
  • [ 6277-86-7 ]
YieldReaction ConditionsOperation in experiment
95% With chloro(1,5-cyclooctadiene)rhodium(I) dimer; copper(II) acetate monohydrate; Trimethylacetic acid; In diethylene glycol dimethyl ether; at 150℃; for 5h;Green chemistry;Catalytic behavior; General procedure: To a 20 mL two-necked flask with a reflux condenser, a drying tube filled with CaCl2, and a rubber cup were added amine 1 (0.5 mmol), [RhCl(cod)]2 (0.01 mmol, 5.0mg), Cu(OAc)2?H2O (0.1 mmol, 20 mg), pivalic acid (0.5 mmol, 51 mg), dibenzyl (ca. 50 mg) as internal standard, and diglyme (3 mL). Then, the resulting mixture was stirred under air 150 °C (bath temperature) for 1-2 h. After cooling, to the reaction mixture was added water (30 mL) and ethylenediamine (2 mL). The mixture was extracted with ethyl acetate (3x30mL) and dried over Na2SO4. After evaporation of the solvents under vacuum, product 2 was isolated by column chromatography using eluent shown below.
  • 40
  • [ 3878-55-5 ]
  • [ 5824-40-8 ]
  • [ 1195771-44-8 ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In acetonitrile; at 20℃; for 24h;pH 9 - 11; To a solution of mono-methyl hydrogen succinate (2, 45mmol) in acetonitrile (50ml) triphenylmethylamine (45mmol) and HBTU (45mmol) were added which was followed by the addition of triethylamine (90mmol). The mixture was stirred at room temperature for 24 h. The pH of the reaction mixture was kept between pH 9 and 11, and adjusted, if necessary, by the addition of triethylamine. After the reaction was completed, the volatile products were evaporated. The resulting oil was dissolved in ethyl acetate (100ml) and washed with 5percent NaHCO3 (2.x.50 ml), brine (50ml), 5percent KHSO4 (2.x.50 ml), brine (50ml) and dried over MgSO4. The solution was filtered and evaporated to dryness. The product was purified using SilicaGel column chromatography.Compound 3, methyl 4-oxo-4-(tritylamino)butanoate: Yield: 30percent; white solid, mp 157oC; Rf = 0.58 (CHCl3:AcOEt/4:1, v:v); HRMS m/z 396.1576/396.1594 (M+Na)+; 1H NMR (300MHz, CDCl3, ppm): delta 2.45-2.72 (m, 4H, 2.x.CH2), 3.65 (s, 3H, CH3), 6.83 (s, 1H, NH), 7.15-7.36 (m, 15H, Ar-H).
  • 41
  • [ 13865-19-5 ]
  • [ 5824-40-8 ]
  • [ 59795-89-0 ]
  • [ 1420536-46-4 ]
  • 42
  • [ 5824-40-8 ]
  • [ 13949-93-4 ]
  • [ 59795-89-0 ]
  • [ 1420536-47-5 ]
  • 43
  • [ 119072-55-8 ]
  • [ 5824-40-8 ]
  • [ 13949-93-4 ]
  • [ 1420536-48-6 ]
  • 44
  • [ 88333-03-3 ]
  • [ 5824-40-8 ]
  • [ 590-86-3 ]
  • [ 1420536-38-4 ]
  • 45
  • [ 931-53-3 ]
  • [ 5824-40-8 ]
  • [ 78-84-2 ]
  • [ 1420536-42-0 ]
YieldReaction ConditionsOperation in experiment
General procedure: <strong>[5824-40-8]Tritylamin</strong>e (2.0 mmol, 1.0 equiv) and aldehyde (3.0 mmol,1.5 equiv) components were mixed in EtOH (2.0 mL) in a sealed vial provided with a magnetic stirring bar. The reaction was heated at 100 C under MW irradiation for 15 minutes.Then, the isocyanide (2.2 mmol, 1.1 equiv) component and azidotrimethylsilane (2.2 mmol, 1.1 equiv, 292 muL) were addedinto the reaction mixture and further heating followed at 100 C under MW irradiation for 15 minutes. The solvent was removedunder reduced pressure and the residue was used for thenext step without any purification.
  • 46
  • [ 931-53-3 ]
  • [ 5824-40-8 ]
  • [ 122-78-1 ]
  • [ 1420536-43-1 ]
YieldReaction ConditionsOperation in experiment
General procedure: <strong>[5824-40-8]Tritylamin</strong>e (2.0 mmol, 1.0 equiv) and aldehyde (3.0 mmol,1.5 equiv) components were mixed in EtOH (2.0 mL) in a sealed vial provided with a magnetic stirring bar. The reaction was heated at 100 C under MW irradiation for 15 minutes.Then, the isocyanide (2.2 mmol, 1.1 equiv) component and azidotrimethylsilane (2.2 mmol, 1.1 equiv, 292 muL) were addedinto the reaction mixture and further heating followed at 100 C under MW irradiation for 15 minutes. The solvent was removedunder reduced pressure and the residue was used for thenext step without any purification.
  • 47
  • [ 931-53-3 ]
  • [ 5824-40-8 ]
  • [ 2043-61-0 ]
  • [ 1420536-44-2 ]
  • 48
  • [ 5824-40-8 ]
  • [ 1079-66-9 ]
  • [ 1425274-91-4 ]
YieldReaction ConditionsOperation in experiment
90% In toluene; at 0 - 20℃;Inert atmosphere; Schlenk technique; In a flame dried Schlenk flask 1.32 g (6.0 mmol) of chlorodiphenylphosphine was dissolved in 5 ml of dry toluene. To this solution, 2.19 g (12.0 mmol) of benzhdrylamine in 5 ml of dry toluene was added dropwise under stirring at 0 C, immediate white turbidity was observed. The solution mixture was stirred for another 3 h at room temperature, and then white precipitate was filtered by using G4 frit and filtrate is collected. Solvent was removed in vacuo; pale yellow colored powder is obtained. Yield was 2.0 g (90percent).
  • 49
  • [ 5824-40-8 ]
  • [ 26726-81-8 ]
  • [ 1427927-32-9 ]
YieldReaction ConditionsOperation in experiment
96% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 60℃; for 2h; Step 4) The dibromo compound 6 (650 mg, 2.0 mmol) was dissolved in DMF (5 mL). DIEA (0.87 mL, 5.0 mmol) and tritylamine (2.1 mmol) was added and the mixture was heated to 60°C and stirred for 2 hours. DMF was removed under vacuum and the residue was taken up with EtOAc (60 mL). The organics was washed with water and brine and dried over Na2S04. After concentration, the residue was purified with column (silica gel, 30percent EtOAc/Hexane) gave the product 7 (806 mg).
  • 50
  • [ 131543-46-9 ]
  • [ 5824-40-8 ]
  • [ 1431932-48-7 ]
YieldReaction ConditionsOperation in experiment
77% In methanol; water; at 20℃;Inert atmosphere; General procedure: To a stirred solution of triphenylmethanamine (1 g, 3.8 mmol) in methanol (15 mL) at ambient temperature was added glyoxal (40 wt.percent solution in water, 0.5 mL, 4 mmol). After being stirred at ambient temperature for overnight, the white precipitate generated was collected by filtration, washed with hexane (5 mL * 2) and dried under vacuum to give 2 as white solid (770 mg, 77percent yield). M.p. 256 °C. FT-IR (selective stretching frequency): 3021(nu, Ar-H), 1622(nu, C=N), 1489 (delta, C-H), cm-1. 1H NMR (400 MHz, CDCl3) delta 7.80 (s, 2H, N=CH), 7.18-7.24(m, 20H, Ph), 7.08-7.17(m, 10H, Ph); 13C NMR (100 MHz, CDCl3) delta 161.7(Imine-C), 144.7(Quaternary-C), 129.8(aromatic-C), 127.9(aromatic-C), 127.1(aromatic-C), 79.4 ((C=N-C); C40H32N2 (540.68): calcd C, 88.85, H, 5.97, N, 5.18; found C, 88.24, H, 5.73, N, 5.10.
  • 51
  • [ 5824-40-8 ]
  • [ 2950-83-6 ]
  • [ 1452393-82-6 ]
YieldReaction ConditionsOperation in experiment
18% With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 17h;Inert atmosphere; General procedure: The relevant carboxylic acid (1equiv), HOBt (1.4equiv) and TBTU (1.4equiv) were dissolved in DMF. To this was added DIPEA (3equiv) and stirred at room temperature for 1 h. To the mixture, the amine (3.2 equiv) was added and the reaction left to stir at room temperature overnight under an atmosphere of Ar. The mixture was diluted with CHCl3 (25mL) and extracted with H2O (5 ×30mL). The organic layer was dried with MgSO4 and the solvent concentrated under reduced pressure. The product was purified by flash chromatography.
  • 52
  • [ 5824-40-8 ]
  • [ 905273-34-9 ]
  • [ 905273-35-0 ]
YieldReaction ConditionsOperation in experiment
40% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 60℃; for 2h; To a suspension of 5-bromo-2,3-bis(bromomethyl)pyridine (1.25 g, 3.64 mmol) in DMF (8 mL) were added triphenylmethanamine (1.41 g, 5.45 mmol) and DIPEA (2.35 g, 18.2 mmol). The reaction was heated at 60 °C for 2 h, and then concentrated in vacuo. The residue was diluted with Eta2Omicron (40 mL) and then extracted with EtOAc (80 mL). The organic phase was washed with brine (50 mL), dried over anhydrous a2S04, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/DCM (v/v) = 2/1) to give the title compound as a pale yellow solid (0.64 g, 40percent).
40% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 60℃; for 2h; 5-Bromo-2,3-bis (bromomethyl) pyridine (1.25 g, 3.64 mmol)Was suspended in N, N-dimethylformamide (8 mL)To this was added triphenylmethylamine (1.41 g, 5.45 mmol) andN, N-diisopropylethylamine (2.35 g, 18.2 mmol).The reaction solution was stirred at 60 ° C for 2 hours and then concentrated under reduced pressure.The residue was diluted with water (40 mL) and extracted with ethyl acetate (80 mL).The organic phase was washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether /Dichloromethane (v / v) = 2/1)The title compound was obtained as a pale yellow solid (0.64 g, 40percent).
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 60℃; for 2.5h; Step 3. Synthesis of 3-bromo-6-trityl-5,7-dihydropyrrolo[3,4-b]pyridine To a solution of 5-bromo-2,3-bis(bromomethyl)pyridine (Step 2 above, 5.6 g, approximately 16.3 mmol) in DMF (40 mL) was added trityl amine (5.3 g, 20.6 mmol) followed by diisopropylethylamine (8.6 mL, 49 mmol). The resulting solution was warmed to 60° C. and stirred at this temperature for 2.5 hr. The mixture was then concentrated under reduced pressure and the residue was purified by silica chromatography (50 g silica, eluted with 10-100percent dichloromethane in hexanes) to give the title compound as a foam.
  • 53
  • [ 5824-40-8 ]
  • [ 127474-54-8 ]
  • (R)-benzyl (1-oxo-1-(tritylamino)pent-4-en-2-yl)carbamate [ No CAS ]
  • 54
  • [ 15761-39-4 ]
  • [ 5824-40-8 ]
  • tert-butyl (2S)-2-(tritylcarbamoyl)pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; A solution of N-t-butyloxycarbonyl-l-proline (2.58 g, 12 mmol) and tritylamine (2.59 mg, 10 mmol) in dry dichloromethane (15 mL) was allowed to stir for 15 min and then cooled to 0 °C after which a dichloromethane (10 mL) solution of dicyclohexylcarbodiimide (2.678 g, 13 mmol) was added. After 20 min, the resulting solution was stirred at room temperature until the complete consumption of the nitroalkene (monitored by TLC). The reaction was quenched with water and extracted with dichloromethane (3 * 100 mL). The combined organic layers were washed with saturated brine solution (100 mL), followed by drying over Na2SO4 and then evaporated in vacuo. The crude product was purified by column chromatography to give pure tert-butyl (S)-2-(tritylcarbamoyl)pyrrolidine-1-carboxylate 4a as an amorphous powder, 96percent yield. [alpha]D20 = -38.4 (c 1.0, CHCl3); IR (KBr) 702, 759, 1164, 1392, 1507, 1695, 2925, 2974, 3321 cm-1; HRMS (EI) calcd for C29H32N2O3 [M+Na]+ 479.2305, found 479.2303. 1H NMR (400 MHz, CDCl3, TMS): delta 8.31 (s, 1H), 7.27-7.21 (m, 15H), 4.48-4.41 (m, 1H), 3.43-3.37 (m, 2H), 2.31 (s, 1H), 1.81-1.76 (m, 5H), 1.42 (s, 9H); 13C NMR (100 MHz, CDCl3, TMS): delta 171.1, 154.1, 144.8, 128.6, 127.9, 126.9, 80.6, 70.2, 58.4, 54.4, 50.1, 47.1, 31.4, 28.4, 28.3, 26.1, 24.6.
  • 55
  • [ 409111-47-3 ]
  • [ 5824-40-8 ]
YieldReaction ConditionsOperation in experiment
General procedure: To a mixture of N-hydroxy-3-phenylpropanamide (1j) (0.198 g, 1.2 mmol), K2CO3 (0.166 g, 1.2 mmol), and DMSO (0.5 mL) was added acetic anhydride (1.1 mL, 0.012 mmol) and heated to 50 °C. After stirring at that temperature for 10 min,the reaction mixture was cooled to 0 °C and then treated with 2 M HCl (ca. 1mL). After the mixture became the clear solution, 2 M NaOH (ca. 2 mL) and di-t-butyl dicarbonate (0.55 mL, 2.4 mmol) was added successively. After stirring for 12 h, the mixture was extracted with Et2O (15 mL x 3). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/Et2O,1:1) to yield t-butyl 3-phenylpropylcarbamate (2j) (0.122 g, 46percent) as a colorless liquid.
  • 56
  • [ 50-00-0 ]
  • [ 5824-40-8 ]
  • [ 39687-95-1 ]
  • methyl 2-(5-((tritylamino)methyl)-1H-tetrazol-1-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: <strong>[5824-40-8]Tritylamin</strong>e (2.0 mmol, 1.0 equiv) and aldehyde (3.0 mmol,1.5 equiv) components were mixed in EtOH (2.0 mL) in a sealed vial provided with a magnetic stirring bar. The reaction was heated at 100 C under MW irradiation for 15 minutes.Then, the isocyanide (2.2 mmol, 1.1 equiv) component and azidotrimethylsilane (2.2 mmol, 1.1 equiv, 292 muL) were addedinto the reaction mixture and further heating followed at 100 C under MW irradiation for 15 minutes. The solvent was removedunder reduced pressure and the residue was used for thenext step without any purification.
  • 57
  • [ 5824-40-8 ]
  • C10H8Br2O2 [ No CAS ]
  • C29H23NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
20.6 g With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 60℃; for 4h;Inert atmosphere; Isoindoline 89. To a suspension of trimethylbenzoic acid (15.0 g, 91.4 mmol, 1.0 equiv), and anhydrous K2C03 (18.8 g, 137 mmol, 1.5 equiv) in DMF (100 mL), Mel (14.3 g, 6.27 mL, 100 mmol, 1.1 equiv) was added dropwise over 3 min under vigorous stirring at room temperature. Upon completion of addition, the reaction mixture was stirred for additional 5 h at room temperature, then poured into 0 (200 mL) and extracted with Et20 (3 x 200 mL). The combined organic layers were washed with water (3 x 100 mL) and brine (2 x 100 mL), dried over MgS04 and concentrated to yield crude product 86 as a colorless oil. Ester 86 and -bromosuccinimide (52.0 g, 292 mmol, 3.2 equiv) were dissolved in CCLt (200 mL), the reaction mixture was heated to 80 °C and benzoyl peroxide (242 mg, 1.0 mmol, 0.02 equiv) was added in one portion. Heating continued for 8 h and the reaction mixture was cooled to ambient temperature, and then stored at 0 °C for 3 h. The reaction mixture was then filtered through a short plug of Celite®, and the precipitates were rinsed with CC14 (0-5 °C). The combined filtrates were then washed with saturated aq. NaHC( (25 mL) and brine (25 mL), dried over MgSO t, and concentrated to yield crude product 87 as a white solid. Neat tribromoester 87 was heated to 150 °C in a slight vacuum for 10 h. The reaction mixture was cooled to ambient temperature and a dark brown solid was obtained as crude product 88. Dibromophthalide 88 was dissolved in DMF (100 mL), z'-Pr2NEt (29.5 g, 39.7 mL, 228 mmol, 2.5 equiv) was added in one portion, followed by tritylamine (23.7 g, 91.4 mmol, 1.0 equiv). The reaction mixture was stirred at 60 °C for 4 h, then poured into 0 (300 mL) and vigorously stirred for 15 min. The precipitates were filtered and rinsed with H20, and dried under vaccum to yield isoindoline 89 as a white solid. The combined filtrates were extracted with EtOAc (3 x 100 mL), and the combined organic layers were washed with water (3 x 50 mL) and brine (2 x 50 mL), dried over MgSC>4 and concentrated. Flash column chromatography (silica gel, CH2Cl2:EtOAc 50: 1 to 20: 1) gave a second portion of isoindoline 89 as a white solid (20.6 g, 49.3 mmol, 54percent yield). 89: R/= 0.47 (silica gel, CH2Cl2:EtOAc 20: 1); IR (film) vmax = 3708, 3681, 2973, 2939, 2923, 2866, 2844, 2826, 1762, 1709, 1614, 1428, 1394, 1350, 1301, 1150, 1126, 1053, 1032, 1008 cm"1; NMR (600 MHz, CDC13): delta = 7.59 (m, 6 H), 7.30 (m, 11 H), 5.21 (s, 2 H), 3.99 (d, J = 7.6 Hz, 4 H) ppm; 1 C NMR (150 MHz, CDC13): delta = 171.0, 145.7, 142.1, 130.1, 129.4, 128.5, 128.0, 127.7, 126.5, 126.4, 119.0, 115.6, 75.1, 69.4, 52.2, 51.6 ppm; HRMS (ESI-TOF): calcd for C29H24N02+ [M+H+] : 418.1802, found 418.1807.
  • 58
  • [ 612-57-7 ]
  • [ 5824-40-8 ]
  • N-tritylquinolin-6-amine [ No CAS ]
  • 59
  • [ 5824-40-8 ]
  • [ 602-56-2 ]
  • 60
  • [ 5824-40-8 ]
  • [ 602-56-2 ]
  • [ 52458-00-1 ]
  • 61
  • [ 5824-40-8 ]
  • [ 5314-37-4 ]
  • C12H10O6S2*2C19H17N*H2O [ No CAS ]
  • 62
  • [ 67-56-1 ]
  • [ 5824-40-8 ]
  • [ 5314-37-4 ]
  • C12H10O6S2*2C19H17N*2H2O*2CH4O [ No CAS ]
  • 63
  • [ 67-56-1 ]
  • [ 5824-40-8 ]
  • [ 5314-37-4 ]
  • C12H10O6S2*2C19H17N*CH4O [ No CAS ]
  • 64
  • [ 64-17-5 ]
  • [ 5824-40-8 ]
  • [ 5314-37-4 ]
  • C12H10O6S2*2C19H17N*C2H6O [ No CAS ]
  • 65
  • [ 71-23-8 ]
  • [ 5824-40-8 ]
  • [ 5314-37-4 ]
  • C12H10O6S2*2C19H17N*3C3H8O [ No CAS ]
  • 66
  • [ 5824-40-8 ]
  • [ 5314-37-4 ]
  • [ 71-36-3 ]
  • C12H10O6S2*2C19H17N*H2O*2C4H10O [ No CAS ]
  • 67
  • [ 5824-40-8 ]
  • [ 5314-37-4 ]
  • [ 71-36-3 ]
  • C12H10O6S2*2C19H17N*2C4H10O [ No CAS ]
  • 68
  • [ 71-41-0 ]
  • [ 5824-40-8 ]
  • [ 5314-37-4 ]
  • C12H10O6S2*2C19H17N*H2O*2C5H12O [ No CAS ]
  • 69
  • [ 71-41-0 ]
  • [ 5824-40-8 ]
  • [ 5314-37-4 ]
  • C12H10O6S2*2C19H17N*2C5H12O [ No CAS ]
  • 70
  • [ 5824-40-8 ]
  • [ 5314-37-4 ]
  • [ 68-12-2 ]
  • C12H10O6S2*2C19H17N*3H2O*2C3H7NO [ No CAS ]
  • 71
  • [ 5824-40-8 ]
  • [ 5314-37-4 ]
  • [ 68-12-2 ]
  • C12H10O6S2*2C19H17N*4C3H7NO [ No CAS ]
  • 72
  • [ 123-91-1 ]
  • [ 5824-40-8 ]
  • [ 5314-37-4 ]
  • C12H10O6S2*2C19H17N*C4H8O2*2C19H17N [ No CAS ]
  • 73
  • [ 5824-40-8 ]
  • [ 5314-37-4 ]
  • [ 67-68-5 ]
  • C12H10O6S2*2C19H17N*4C2H6OS [ No CAS ]
  • 74
  • [ 5824-40-8 ]
  • [ 76-05-1 ]
  • 2,2,2-trifluoro-N-(trityl)ethanimidoyl chloride [ No CAS ]
  • 75
  • [ 34906-91-7 ]
  • [ 5824-40-8 ]
  • C26H27NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
539.3 mg With 4-methyl-morpholine; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; In dichloromethane; at 20℃; for 10h; To a solution of crude S8a in CH2Cl2 (20 ml) was added N-methylmorpholine (420 mul, 3.82 mmol),trityl amine (991 mg, 3.82 mmol), and COMU (982 mg, 2.29 mmol) sequentially at roomtemperature. The mixture was stirred for 10 h at the same temperature before quenching withdistilled water. The resulting mixture was extracted with CH2Cl2 twice. The combined organic layerswere dried over MgSO4 and concentrated in vacuo. Further purification was carried out by silica gelcolumn chromatography to give alpha-ketoamide 16a (539.3 mg, 54percent in 3 steps) as a white amorphoussolid.
  • 76
  • [ 5824-40-8 ]
  • C13H16O4 [ No CAS ]
  • C32H31NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
417 mg With 4-methyl-morpholine; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; In dichloromethane; at 20℃; for 10h; General procedure: To a solution of crude S8a in CH2Cl2 (20 ml) was added N-methylmorpholine (420 mul, 3.82 mmol),trityl amine (991 mg, 3.82 mmol), and COMU (982 mg, 2.29 mmol) sequentially at roomtemperature. The mixture was stirred for 10 h at the same temperature before quenching withdistilled water. The resulting mixture was extracted with CH2Cl2 twice. The combined organic layerswere dried over MgSO4 and concentrated in vacuo. Further purification was carried out by silica gelcolumn chromatography to give alpha-ketoamide 16a (539.3 mg, 54percent in 3 steps) as a white amorphoussolid.
  • 77
  • [ 5824-40-8 ]
  • C8H14O3 [ No CAS ]
  • C27H29NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
311.6 mg With 4-methyl-morpholine; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; In dichloromethane; at 20℃; for 5h; To a solution of crude alpha-ketoacid (S8g, 190 mg, 1.20 mmol) in CH2Cl2 (12 ml) was addedN-methylmorpholine (264 mul, 2.40 mmol), trityl amine (622 mg, 2.40 mmol), and COMU (617 mg,1.44 mmol) sequentially at room temperature. The mixture was stirred for 5 h at the sametemperature before quenching with a distilled water. The resulting mixture was extracted withCH2Cl2 twice. The combined organic layers were dried over MgSO4 and concentrated in vacuo.Further purification was carried out by silica gel column chromatography to give alpha-ketoamides 16g(311.6 mg, 14percent in 5 steps) as a white amorphous solid.
  • 78
  • [ 5824-40-8 ]
  • [ 815-17-8 ]
  • C25H25NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With 4-methyl-morpholine; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; In dichloromethane; at 20℃; for 9h; To a solution of 3,3-dimethyl-2-oxobutyric acid (S1, 133 mg, 1.02 mmol) in CH2Cl2 (2 ml) wasadded N-methylmorpholine (224 mul, 2.04 mmol), trityl amine (530 mg, 2.04 mmol) and COMU (525mg, 1.23 mmol) sequentially at room temperature. The mixture was stirred for 9 h at the sametemperature before quenching with distilled water. The resulting mixture was extracted with CH2Cl2twice. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Furtherpurification was carried out by silica gel column chromatography to give alpha-ketoamides 14f (332 mg,87percent) as a white amorphous solid.
  • 79
  • [ 5824-40-8 ]
  • [ 359804-14-1 ]
  • C28H29NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
216 mg With 4-methyl-morpholine; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; In dichloromethane; at 20℃; for 5.5h; To a solution of crude S8h (798 mg) in CH2Cl2 (25 ml) was added N-methylmorpholine (473 mul,4.20 mmol), trityl amine (1.09 g, 4.20 mmol), and COMU (1.08 g, 2.52 mmol) sequentially at roomtemperature. The mixture was stirred for 5.5 h at the same temperature before quenching withdistilled water. The resulting mixture was extracted with CH2Cl2 twice. The combined organic layerswere dried over MgSO4 and concentrated in vacuo. Further purification was carried out by silica gelcolumn chromatography to give alpha-keto amide 16h (216 mg, 25percent in 3 steps) as a white amorphous solid.
  • 80
  • [ 50-00-0 ]
  • [ 5824-40-8 ]
  • [ 51642-06-9 ]
  • methyl 4-(5-((tritylamino)methyl)-1H-tetrazol-1-yl)butanoate [ No CAS ]
  • 81
  • [ 50-00-0 ]
  • [ 5824-40-8 ]
  • C8H13NO2 [ No CAS ]
  • methyl 6-(5-((tritylamino)methyl)-1H-tetrazol-1-yl) hexanoate [ No CAS ]
  • 82
  • [ 41014-43-1 ]
  • [ 5824-40-8 ]
  • triphenylmethyl{N-(benzooxazolylmethyl)}amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 80℃; In single-port bottle by adding triphenyl methylamine (2.32g, 8 . 95mmol), 2-chloro-methyl and oxazoline (1.50g, 8 . 95mmol), potassium carbonate (1.36g, 9 . 85mmol), potassium iodide (297 mg, 1 . 79mmol) and 25mLN, after N-dimethyl formamide, for 80 C lower reaction sleepovers. Water quenching the reaction, ethyl acetate extraction, combined with the phase, drying, filtering, evaporating solvent under reduced pressure. Residual oil-shaped column chromatography (silica gel, petroleum ether: ethyl acetate = 20:1) obtaining white transparent oily separation and purification (2.60g, 75%).
  • 83
  • [ 104-53-0 ]
  • [ 5824-40-8 ]
  • [3-Phenyl-prop-(E)-ylidene]-trityl-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With tetrabutoxytitanium; In toluene; for 5h;Reflux; The 3-phenylpropanal(55g, 0.41mol) were added to toluene (400ml), followed by addition of triphenylmethylamine (106.2g, 0.41mol) and tetrabutyl titanate (278.8g, 0.82mol), stirred for 1 hour at room temperature , then refluxed for 4 hours, TLC the reaction was complete feed point detection plate, cooled to room temperature, saturated sodium bicarbonate, stirred, allowed to stand, stratification, the organic phase was separated, concentrated under reduced pressure, the residue was added ethyl acetate and saturated aqueous sodium chloride esters, extraction, standing layer, the organic phase was separated, dried over anhydrous sodium sulfate, the drying agent was removed by filtration, concentrated under reduced pressure to give the crude compound II, ethyl acetate: petroleum ether = 3: 7 (volume ratio ) to give an off-white solid was recrystallized compound II103.1g, yield 74percent.
  • 84
  • [ 5824-40-8 ]
  • [ 2900-27-8 ]
  • tert-butyl (S)-(2-oxo-1-phenyl-2-(tritylamino)ethyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% General procedure: At first,EDCI (1.22 g, 5.5 mmol) was added into a stirring solution of(tert-butoxycarbonyl)leucine 10 (1.16 g, 5.0 mmol) and DMAP(210 mg, 1.5 mmol) in dry dichloromethane (15 mL). The mixturewas stirred for 15 min and then cooled to 0 C. Triphenylmethanamine11a (1.04 g, 4 mmol) was added to the mixtureand stirred at the same temperature for 30 min. The resulting solutionwas stirred at room temperature until complete consumptionof triphenylmethanamine (monitored by TLC). The reaction wasquenched with water (50 mL) and extracted with dichloromethane(3 50 mL). The combined organic layers were washed with saturatedbrine solution (30 mL), followed by drying over Na2SO4 andevaporation in vacuo. The crude product was purified by columnchromatography to give pure tert-butyl (S)-(4-methyl-1-oxo-1-(tritylamino)pentan-2-yl)carbamate 12a.
  • 85
  • [ 5824-40-8 ]
  • [ 13734-34-4 ]
  • tert-butyl (S)-(1-oxo-3-phenyl-1-(tritylamino)propan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% General procedure: At first,EDCI (1.22 g, 5.5 mmol) was added into a stirring solution of(tert-butoxycarbonyl)leucine 10 (1.16 g, 5.0 mmol) and DMAP(210 mg, 1.5 mmol) in dry dichloromethane (15 mL). The mixturewas stirred for 15 min and then cooled to 0 C. Triphenylmethanamine11a (1.04 g, 4 mmol) was added to the mixtureand stirred at the same temperature for 30 min. The resulting solutionwas stirred at room temperature until complete consumptionof triphenylmethanamine (monitored by TLC). The reaction wasquenched with water (50 mL) and extracted with dichloromethane(3 50 mL). The combined organic layers were washed with saturatedbrine solution (30 mL), followed by drying over Na2SO4 andevaporation in vacuo. The crude product was purified by columnchromatography to give pure tert-butyl (S)-(4-methyl-1-oxo-1-(tritylamino)pentan-2-yl)carbamate 12a.
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