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CAS No. : | 949-90-6 | MDL No. : | MFCD00042825 |
Formula : | C10H12N2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HQYMUNCIMNFLDT-UHFFFAOYSA-N |
M.W : | 208.21 | Pubchem ID : | 70366 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 53.21 |
TPSA : | 81.42 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) : | -7.3 cm/s |
Log Po/w (iLOGP) : | 1.43 |
Log Po/w (XLOGP3) : | 0.38 |
Log Po/w (WLOGP) : | 0.25 |
Log Po/w (MLOGP) : | 0.45 |
Log Po/w (SILICOS-IT) : | 0.34 |
Consensus Log Po/w : | 0.57 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.27 |
Solubility : | 11.2 mg/ml ; 0.0537 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.66 |
Solubility : | 4.6 mg/ml ; 0.0221 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.54 |
Solubility : | 0.595 mg/ml ; 0.00286 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.99 |
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 |
---|---|---|
79% | With Lawessons reagent; In 1,4-dioxane; at 20 - 60℃; for 4.5 - 4.75h; | Synthesis of Compound A.2. To a solution of compound A.1 (0.5 g, 0.0024 mol) in dioxane (7 mL) was added Lawesson's reagent (0.5 g, 0.0013 mol). The reaction was heated at 60 C. for 30-45 min. The reaction was brought to RT and stirred for an additional 4 hr. Dioxane was removed under reduced pressure. The reaction mixture was diluted with EtOAc (3 mL) and the organic layer was washed with sat. NaHCO3 (2 mL). The aqueous layer was again extracted with EtOAc (2×5 mL). The combined organic extracts were again washed with sat. NaHCO3 (3×5 mL), dried (Na2SO4) and concentrated under reduced pressure to furnish compound A.2 as a light yellow solid (0.42 g, 79%). 1H NMR: (CDCl3-DMSO-d6, 200 MHz) delta: 7.4 (s, 5H), 6.4 (1H, D2O exchangeable), 5.2 (s, 2H), 4.2 (d, 2H, J=5 Hz); MS: m/z 224.9 [M+1]+. |
79% | With Lawessons reagent; In 1,4-dioxane; at 20 - 60℃; for 4.5 - 4.75h; | To a solution of compound A.1 (0.5 g, 0.0024 mol) in dioxane (7 mL) was added Lawesson's reagent (0.5 g, 0.0013 mol). The reaction was heated at 60 C. for 30-45 min. The reaction was brought to RT and stirred for an additional 4 hr. Dioxane was removed under reduced pressure. The reaction mixture was diluted with EtOAc (3 mL) and the organic layer was washed with sat. NaHCO3 (2 mL). The aqueous layer was again extracted with EtOAc (2×5 mL). The combined organic extracts were again washed with sat. NaHCO3 (3×5 mL), dried (Na2SO4) and concentrated under reduced pressure to furnish compound A.2 as a light yellow solid (0.42 g, 79%). 1H NMR: (CDCl3-DMSO-d6, 200 MHz) delta: 7.4 (s, 5 H), 6.4 (1 H, D2O exchangeable), 5.2 (s, 2 H), 4.2 (d, 2 H, J=5 Hz); LCMS: m/z 224.9 [M+1]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With candida antarctica lipase-B; ammonium benzoate; In toluene; at 50℃; for 16h;Molecular sieve; Enzymatic reaction; | General procedure: Cal-B (100 mg) was added to a mixture of Cbz-Xaa-OH (50 mg), ammonium benzoate (10 equiv) and 3 A MS (200 mg) in toluene (6 mL). The mixture was shaken at 50 C, 150 rpm for 16 h. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With trifluoroacetic acid; In ethanol; dichloromethane; ethyl acetate; | A suspension of 2.5 g (0.0044 mol) of (1i) in dichloromethane (10 ml) was cooled with an ice bath and 10 ml of trifluoroacetic acid was added. The homogeneous solution was stirred at ca. 5 C. for 20 minutes, then allowed to warm to room temperature. After 90 minutes the dichloromethane and trifluoroacetic acid were removed in vacuo. The resulting residue was dissolved in 100 ml of ethyl acetate and washed with 2M NaOH (3*50 ml), water (50 ml) and brine (50 ml). The non-homogeneous solution was transferred to a flask containing 100 ml of absolute ethanol, and heated until it became homogeneous. The hot solution was dried over a small amount of anhydrous sodium sulfate, filtered, and concentrated in vacuo to obtain a solid. The solid was triturated with cold 1:3 ethyl acetate-hexane and collected by filtration to give 1.46 g (71% yield) of L-3-(2'-naphthyl)alanyl-L-alanine, 2-(benzyloxy-carbonyl-amino)ethyl amide (1j) as a white solid. 1 H NMR (CDCl3) delta 1.33(d, 3H), 1.60(bs, 2H), 2.83(m, 1H), 3.34(m, 5H), 3.82(m, 1H), 4.44(m, 1H), 5.07(s, 2H), 5.33(t, 1H), 6.92(t, 1H), 7.31(bs, 5H), 7.36(s, 1H), 7.48(m, 2H), 7.65(s, 1H), 7.72(d, 1H), 7.81(m, 3H); 13 C NMR (CDCl3) delta 17.6, 40.6, 40.7, 40.9, 48.6, 56.1, 66.9, 125.4, 125.8, 127.2, 127.4, 127.5, 127.8, 127.9, 128.4, 132.4, 133.4, 135.1, 136.5, 156.1, 172.7, 174.7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With 4-methyl-morpholine; In ethyl acetate; N,N-dimethyl-formamide; | Under an atmosphere of dry argon, a solution of 8.9 g (0.028 mol) of N-BOC-L-3-(2'-naphthyl)alanine and 3.2 ml (0.028 mol) of 4-methylmorpholine in anhydrous N,N-dimethylformamide (20 ml) was cooled to -15 C. and treated with 3.67 ml (0.028 mol) of isobutyl chloroformate. The mixture was stirred at -15 C. for 30 minutes, then a solution of 7.5 g (0.028 mol) of (1h) and 3.2 ml (0.028 mol) of 4-methylmorpholine in anhydrous N,N-dimethylformamide (20 ml) was added slowly, over 10 minutes. The reaction was stirred at -15 C. for 2 hours, then at room temperature for 18 hours. The N,N-dimethylformamide was removed in vacuo and the resulting solid was dissolved in 1 liter of hot ethyl acetate. The hot solution was washed with 1M HCl (3*150 ml), water (150 ml), saturated sodium bicarbonate (3*150 ml) and finally with brine (150 ml). After drying over anhydrous magnesium sulfate, the hot solution was concentrated in vacuo. The resulting yellow solid was triturated with 400 ml of cold 1:3 ethyl acetate-hexane and collected by filtration to give 14.5 g (91% yield) of N-BOC-L-3-(2'-naphthyl)alanyl-L-alanine, 2-(benzyloxycarbonylamino)ethyl amide (1i) as a white solid. TLC: Rf 0.59 (chloroform-isopropanol 9:1); 1 H NMR(CDCl3) delta 1.26(d, 3H), 1.35(s, 9H), 3.16(m, 6H), 4.42(m, 1H), 4.50(m, 1H), 5.07(s, 2H), 5.25(d, 1H), 5.69(m, 1H), 6.82(m, 1H), 6.90(d, 1H), 7.29(s, 1H), 7.31(bs, 5H), 7.45(m, 2H), 7.61(s, 1H), 7.76(m, 3H); 13 C NMR (CDCl3) delta 18.0, 28.2, 38.2, 39.7, 40.6, 49.0, 55.9, 66.6, 80.6, 125.8, 126.2, 127.2, 127.5, 127.6, 127.9, 128.0, 128.4, 132.4, 133.3, 133.8, 134.2, 155.4, 156.7, 171.4, 172.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7.72 g (3.16%) | With sodium bicarbonate; In toluene; | A) Isobutyl (E)-1-benzyloxycarbonyl-4-oxo-2-imidazolidineacrylate To a solution of isobutyl (E)-4-oxo-2-butenoate (11 g, 70.43 mmol) in toluene (170 ml) <strong>[949-90-6]benzyloxycarbonyl-glycinamide</strong> (14.67 g, 70.43 mmol) and p-toluensulfonic acid monohydrate (0.67 g, 3.5 mmol) were added. The mixture was refluxed for 4 hours in a Dean-Stark apparatus. The obtained solution was cooled, the precipitate matter was filtered off and the filtrate was washed with a saturated solution of sodium hydrogen carbonate (50 ml) and brine (50 ml). The organic phase, dried over anhydrous sodium sulfate, was evaporated to dryness. The residue was chromatographed over silica gel (ethyl acetate-cyclohexane 1:1). The collected fractions were evaporated and the residue, triturated with diisopropyl ether, afforded 7.72 g (3.16%) of the title compound as a white solid, m.p. 97-100 C. NMR (CDCl3): deltaH =6.80 (ABX, JAB =15 Hz, JAX =7 Hz, 1H, CH=CH--CO), 6.15 (c.a., 1H, CH=CH--CO), 5.70 (ABX, JAB =7 Hz, CH=CH--CH), 4.10 and 3.97 (ABq, J=16 Hz, 2H, COCH2 N). MS (E.I., 70 eV, 1.5 mA) m/z=346 (M+), 239 (M--C7 HO)+, 91 (C7 H7+). |
7.72 g (31.6%) | With sodium bicarbonate; In toluene; | A) Isobutyl (E)-1-benzyloxycarbonyl-4-oxo-2-imidazolidineacrylate To a solution of isobutyl (E)-4-oxo-2-butenoate (11 g, 70.43 mmol) in toluene (170 ml) benzyloxycarbonylglycinamide (14.67 g, 70.43 mmol) and p-toluensulfonic acid monohydrate (0.67 g, 3.5 mmol) were added. The mixture was refluxed for 4 hours in a Dean-Stark apparatus. The obtained solution was cooled, the precipitate matter was filtered off and the filtrate was washed with a saturated solution of sodium hydrogen carbonate (50 ml) and brine (50 ml). The organic phase, dried over anhydrous sodium sulfate, was evaporated to dryness. The residue was chromatographed over silica gel (ethyl acetate-cyclohexane 1:1). The collected fractions were evaporated and the residue, triturated with diisopropyl ether, afforded 7.72 g (31.6%) of the title compound as a white solid, m.p. 97-100C. NMR (CDCl3): deltaH= 6.80 (A BX, JAB=15 Hz, JAX=7 Hz, 1H, C H =CH-CO), 6.15 (c.a., 1H, CH=C H -CO), 5.70 (AB X , JAB= 7 Hz, C H =CH-CH), 4.10 and 3.97 (ABq, J=16 Hz, 2H, COC H 2N). MS (E.I., 70 eV, 1.5 mA) m/z = 346 (M+), 239 (M-C7H7O)+, 91 (C7H7+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 16h;Inert atmosphere; | General procedure: In a flame-dried Schlenk tube, palladium acetate (0.017 mmol, 0.1 eq), Xantphos (0.035 mmol, 0.1 eq) and Cs2CO3 (0.530 mmol, 1.5 eq) were introduced under Argon. The Schlenk tube was purged few minutes with Argon. A solution of benzophenone (0.350 mmol, 1 eq) and the glycinamide derivative (0.420 mmol, 1.2 eq) in dioxane (1 mL) was added. The mixture was stirred at 100 C (16 h). The solution was filtered through a pad of celite. The pad was washed with CH2Cl2. The organic layers were combined and the solvents were evaporated. The residue was purified by silica gel column chromatography (cyclohexane/EtOAc) to obtain the coupled compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 16h;Inert atmosphere; | General procedure: In a flame-dried Schlenk tube, palladium acetate (0.017 mmol, 0.1 eq), Xantphos (0.035 mmol, 0.1 eq) and Cs2CO3 (0.530 mmol, 1.5 eq) were introduced under Argon. The Schlenk tube was purged few minutes with Argon. A solution of benzophenone (0.350 mmol, 1 eq) and the glycinamide derivative (0.420 mmol, 1.2 eq) in dioxane (1 mL) was added. The mixture was stirred at 100 C (16 h). The solution was filtered through a pad of celite. The pad was washed with CH2Cl2. The organic layers were combined and the solvents were evaporated. The residue was purified by silica gel column chromatography (cyclohexane/EtOAc) to obtain the coupled compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of <strong>[949-90-6]benzyl (2-amino-2-oxoethyl)carbamate</strong> (8.5 g, 40.8 mmol) in CH2Cl2 (204 mL) was added trimethyloxonium tetrafluoroborate (6.0 g, 40.8 mmol) in one portion. The resulting mixture was stirred for 24 h, then acidified to pH3 with 1N ethereal HCl. The resulting mixture was concentrated under reduced pressure to yield methyl 2-(((benzyloxy)carbonyl)amino)acetimidate. A solution of methyl 2-(((benzyloxy)carbonyl)amino)acetimidate (9.3 g, 36 mmol), 4-(benzyloxy)benzothiohydrazide (8.0 g, 24 mmol) and diisopropylethylamine (4.2 mL, 24 mmol) in methanol (480 mL) was refluxed for 12 h. The resulting mixture was cooled to room temperature, at which point benzyl ((5-(4-(benzyloxy)phenyl)-1,3,4-thiadiazol-2-yl)methyl)carbamate precipitated and was collected (MS m/z=432 MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | In 1-methyl-pyrrolidin-2-one; at 100℃; for 6h;Inert atmosphere; | In a round bottom flask a mixture of <strong>[949-90-6]benzyl 2-amino-2-oxoethylcarbamate</strong> (59; 3.9 g, 18.80 mmol) and 2-bromoacetophenone (1.5 g, 7.52 mmol) in 6 ml of N-methyl-2-pyrrolidone (NMP) was heated for 6 h at 100 C under N2. After cooling, the crude mixture was diluted with AcOEt (150 ml), washed with aq. NaHCO3 (5% w/v), water, brine, and dried over anhydrous Na2SO4. The organic phase was evaporated to dryness and the crude residue was purified by CC on silica gel (AcOEt/cyclohexane; 25:75). The resulted solid was rinsed with petroleum ether/diethyl ether (8:2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | General procedure: To a solution of an N-Cbz-2-aminoalkanamide 1 (3.0 mmol) and aldehyde 2 (3.5 mmol) in dried acetonitrile (15 mL) was added aryldichlorophosphine 3 (4.0 mmol) under stirring and a nitrogen atmosphere. After the N-Cbz-2-aminoalkanamide 2 was dissolved completely, the resulting solution was stirred in refluxing acetonitrile at 80 C for 1 h. The reaction mixture was allowed to cool to room temperature under stirring. Hydroxyl ester 6 or ethanol (6.0 mmol) was added dropwise. After stirring for 15 min, triethylamine (1.67 mL, 1.22 g, 12 mmol) was added dropwise and the resulting reaction mixture was stirred for another 6 h. After removal of the solvent, the residue was dissolved in ethyl acetate. The solution was washed with saturated aqueous sodium bicarbonate (50 mL×3), saturated brine (50 mL×2), and dried over anhydrous sodium sulfate. After concentration at reduced pressure, the residue was separated on a silica gel column with a mixture of petroleum ether (30-60 C) and ethyl acetate as an eluent with gradient elution to give the desired product phosphinodepsipeptide 7. (Caution: The silica gel column was buffered by 0.5% triethylamine before the sample was loaded. The desired peptide 7 shows very weak fluorescent intensity under UV light. It is better to monitor collective fractions in the column separation after concentration). The aqueous solution was adjusted to pH 1 with 6 mol/L HCl and extracted with ethyl acetate (50 mL×3), the organic phase was dried over anhydrous sodium sulfate. After concentration at reduced pressure, the residue was crystallized from a mixture of ethyl acetate and hexanes or methanol (ethanol) and diethyl ether to afford the corresponding phosphinic acid 5. |
Tags: 949-90-6 synthesis path| 949-90-6 SDS| 949-90-6 COA| 949-90-6 purity| 949-90-6 application| 949-90-6 NMR| 949-90-6 COA| 949-90-6 structure
[ 1138-80-3 ]
2-(((Benzyloxy)carbonyl)amino)acetic acid
Similarity: 0.85
[ 77987-49-6 ]
Benzyl (2-hydroxyethyl)carbamate
Similarity: 0.85
[ 66674-16-6 ]
(S)-Benzyl (1-hydroxypropan-2-yl)carbamate
Similarity: 0.82
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H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
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 |
H330 | Fatal if inhaled |
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 |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
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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