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CAS No. : | 5888-91-5 | MDL No. : | MFCD00021748 |
Formula : | C5H9NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SVXPSKKRNACRPB-UHFFFAOYSA-N |
M.W : | 131.13 | Pubchem ID : | 10975514 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.6 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 31.02 |
TPSA : | 57.61 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) : | -7.58 cm/s |
Log Po/w (iLOGP) : | 0.85 |
Log Po/w (XLOGP3) : | -0.68 |
Log Po/w (WLOGP) : | -0.45 |
Log Po/w (MLOGP) : | -0.54 |
Log Po/w (SILICOS-IT) : | -0.91 |
Consensus Log Po/w : | -0.34 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.85 |
Log S (ESOL) : | -0.03 |
Solubility : | 123.0 mg/ml ; 0.941 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.06 |
Solubility : | 115.0 mg/ml ; 0.88 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.32 |
Solubility : | 273.0 mg/ml ; 2.08 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.01 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-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 |
---|---|---|
und Umsetzung des erhaltenen Methylesters mit wss.NH3; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With sodium hydrogencarbonate In water at 0 - 20℃; for 5h; | |
With benzene | ||
In acetic acid |
In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dicyclohexyl-carbodiimide In nitromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
for 1.5h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With dicobalt octacarbonyl; hydrogen In ethyl acetate at 120℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
electroysis; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | In benzene Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With triphenylphosphine In toluene for 32h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With triethylphosphine for 1h; Ambient temperature; solvent is anh. benzene or diethyl ether; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | With acetic anhydride In toluene at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic anhydride In toluene at 80℃; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With dicyclohexyl-carbodiimide In dichloromethane; <i>tert</i>-butyl alcohol for 3h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With trifluoroacetic acid In dichloromethane for 3h; Ambient temperature; | |
92% | With trifluoroacetic acid In dichloromethane for 2h; Ambient temperature; | |
100 mg | With trifluoroacetic acid In dichloromethane at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With dicyclohexyl-carbodiimide In dichloromethane for 5h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With dmap; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Rk. mit hydratisierten e-; | ||
Tab.I; | ||
Blitz-Photolyse (Kinetik): Geschw.Konst. (Zerfall); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With dicyclohexyl-carbodiimide In 1,2-dimethoxyethane for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water In dimethyl sulfoxide at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With dacarbazine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | Stage #1: N-acetylsarcosine With dacarbazine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide for 0.25h; Stage #2: 2-oxo-9-thia-3,12-diazatricyclo[8.2.1.03,7]tridecane-4-carboxylic acid In dichloromethane; N,N-dimethyl-formamide for 6h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: HATU; DIC / dimethylformamide; CH2Cl2 / 0.25 h 1.2: 36 percent / dimethylformamide; CH2Cl2 / 6 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 2: 81 percent / benzene / 3.5 h / 20 - 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 2: 80 percent / CH2Cl2 / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 2: 70 percent / CH2Cl2 / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 67 percent / N,N'-dicyclohexylcarbodiimide / 1,2-dimethoxy-ethane / 0.5 h 2.1: t-BuOK / 2-methyl-propan-2-ol / 1 h / 20 °C 2.2: 28 percent / 2-methyl-propan-2-ol / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 67 percent / N,N'-dicyclohexylcarbodiimide / 1,2-dimethoxy-ethane / 0.5 h 2.1: t-BuOK / 2-methyl-propan-2-ol / 1 h / 20 °C 2.2: 38 percent / 2-methyl-propan-2-ol / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 67 percent / N,N'-dicyclohexylcarbodiimide / 1,2-dimethoxy-ethane / 0.5 h 2.1: t-BuOK / 2-methyl-propan-2-ol / 1 h / 20 °C 2.2: 71 percent / 2-methyl-propan-2-ol / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 98 percent / DCC / CH2Cl2 / 5 h / Ambient temperature 2: 98 percent / H2 / Pd-C / methanol / 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 98 percent / DCC / CH2Cl2 / 5 h / Ambient temperature 2: 98 percent / H2 / Pd-C / methanol / 3 h 3: 92 percent / DCC / CH2Cl2 / 2 h / Ambient temperature 4: NaOCH3 / methanol / 2 h / Ambient temperature; pH 9 5: TFA / CH2Cl2 / 1 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 98 percent / DCC / CH2Cl2 / 5 h / Ambient temperature 2: 98 percent / H2 / Pd-C / methanol / 3 h 3: 92 percent / DCC / CH2Cl2 / 2 h / Ambient temperature 4: NaOCH3 / methanol / 2 h / Ambient temperature; pH 9 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 98 percent / DCC / CH2Cl2 / 5 h / Ambient temperature 2: 98 percent / H2 / Pd-C / methanol / 3 h 3: 92 percent / DCC / CH2Cl2 / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With H2; CO; acetic acid | 15.C Example 15 C) A 1 L autoclave was charged with N-methylacetamide (IX) (160 g, 2.2 mole), Co(OAc)2 *4H2 O (33 g, 0.13 mole), and acetic acid (1 L). After sealing the autoclave, 2200 psi (15,172 kPa) CO:H2 (70:30) was established at 25° C. with stirring at 2000 rpm. The contents of the autoclave were heated to 1300C and 3200 psi (22,069 kPa) CO:H2 (70:30) was established. After approximately 0.5 h, rapid gas uptake was observed. The reaction mass was cooled to 85° C. Under a constant 3200 psi (22,069 kPa), 47 Wt. % formalin (180 mL, 2.97 mole) was delivered at 6 mL/min. The reaction was stirred at 85° C. for 30 min. after the formalin addition was complete. Then the reaction was cooled to 25° C., removed from the autoclave, and assayed for N-acetylsarcosine. This resulted in a 92% yield of (XX). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-methyl-morpholine; 1-methyl-pyrrolidin-2-one | 29 PREPARATION 29 PREPARATION 29 Pivaloyl chloride (0.22 ml) was added dropwise to a mixture of acetylsarcosine (264 mg), N-methylmorpholine (0.22 ml) and N-methylpyrrolidone (30 ml) under a dry ice-tetrachloromethane bath cooling. This mixture was stirred for 10 minutes under ice-cooling, and 8-[3-amino-2,6-dichlorobenzyloxy]-2-methylimidazo[1,2-a]pyridine (500 mg) was added thereto under a dry ice-tetrachloromethane bath cooling. The mixture was stirred for 22 hours at ambient temperature. The mixture was partitioned between ethyl acetate and a saturated aqueous sodium bicarbonate solution, and the aqueous layer was extracted with ethyl acetate twice. The combined organic layer was dried over magnesium sulfate and concentrated in vacuo, and the residue was purified by flash column chromatography (methylene chloride:methanol=50:1, V/V) to give 8-[3-(acetylsarcosylamino)-2,6-dichlorobenzyloxy]-2-methylimidazo[1,2-a]pyridine (260 mg). NMR (CDCl3, δ): 2.18 (3H, s), 2.42 (3H, s), 3.09 (0.3H, s), 3.19 (2.7H, s), 4.19 (2H, s), 5.45 (2H, s), 6.55-6.72 (2H), 7.30 (1H, s), 7.34 (1H, d, J=9 Hz), 7.72 (1H, d, J=8 Hz), 8.38 (1H, d, J=9 Hz), 8.81 (1H, br s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In 1,4-dioxane; bis-tetrahydropyran ether | B N-Acetyl-Sarcosine Preparation B N-Acetyl-Sarcosine 4-Dimethylaminopyridine (3.66 g) was added to a solution of sarcosine (26.7 g) and triethylamine (50 ml) in (1:1) dioxane water (150 ml) cooled at 0° C. A solution of acetyl chloride (22.37 ml) in dioxane (20 ml) was added dropwise over a period of 30 min. The reaction solution was then stirred at room temperature for 1 hour and subsequently was acidified to pH 3 with cold 50% aqueous HCl. The mixture was extracted three times with ethyl acetate. The extracts were washed with a saturated NaCl solution, dried over Na2 SO4 and concentrated. The residue was crystallized from ethyl acetate to give N-acetyl-sarcosine, m.p. 135°-137° C. Fab Mass spec. m/e 132 (M+H); Anal. for C5 H9 NO3, Calcd: C, 45.79; H, 6.91; N, 10.68; Found: C, 45.78; H, 7.03; N, 10.64. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In pyridine | 1 N-Acetyl-N-methylglycyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-alanyl-L-leucyl-L-arginyl-L-proline ethylamide EXAMPLE 1 N-Acetyl-N-methylglycyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-alanyl-L-leucyl-L-arginyl-L-proline ethylamide In 0.5 ml of dry pyridine were dissolved 40 mg of N-acetyl-N-methylglycine (m.p. 139° - 140° C) and 140 mg of p-nitrophenyl trifluoroacetate, and the solution was left at room temperature for 2 hours. Completion of the reaction for the formation of N-acetyl-N-methylglycine p-nitrophenylester was confirmed by means of thin layer chromatography, and then the solvent was distilled off under reduced pressure. To the residue was added 5 ml of water, and extraction was made with ethyl acetate. The extract was repeatedly washed with water until the water portion became neutral. The extract was dried over anhydrous sodium sulfate and evaporated to leave acetyl-N-methylglycine p-nitrophenylester as an oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; hydrogenchloride; sodium hydrogencarbonate; trifluoroacetic anhydride; zinc In dichloromethane; acetic acid; ethyl acetate | 42 7β-Phenoxyacetamido-6αH-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-4-carboxylic acid EXAMPLE 42 7β-Phenoxyacetamido-6αH-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-4-carboxylic acid To a cooled solution (0° C) of 0.477 g (1 mmol) of trichloroethyl 7β-phenoxyacetamido-6αH-2-hydroxy-8-oxo-4-thia-1-azabicyclo[4.2.0]octane-2-carboxylate in 10 ml ethyl acetate is added 65 μl of trifluoroacetic anhydride and then 362 μl of pyridine. The reaction is stirred overnight at room temperature and then diluted with ethyl acetate. The solution is washed with NaHCO3 solution, 3N HCl and saturated saline solution. The dried solution is evaporated to give the ester of the title product which is recrystallized from benzene; 157 mg (34%). In 24 ml solution of dimethylformamide-glacial acetic acid (1:1) is dissolved 70 mg of the above ester. To this solution is added over a 1.5 hour period 500 mg of zinc dust which has been treated with 5% HCl for 3 minutes, washed with water, ethanol, and ether and then dried. The reaction mixture is stirred 3 hours at room temperature, diluted with water, acidified with 3N HCl and extracted with ethyl acetate. The extracts are washed with a large volume of 5% NaHCO3. The aqueous solution is acidified to pH 2 with HCl and extracted with ethyl acetate. The dried extracts are concentrated in vacuo and then high vacuum is used to remove residual acetic acid. The residue is triturated with ether-hexane, dissolved in methylene chloride and precipitated with hexane to give the title product, mp 194°-5° (dec). | |
With pyridine; hydrogenchloride; sodium hydrogencarbonate; trifluoroacetic anhydride; zinc In dichloromethane; acetic acid; ethyl acetate | 42 7β-Phenoxyacetamido-6αH-8-oxo-4-thia-1-azabicyclo[4.2.0.]oct-2-ene-4-carboxylic acid EXAMPLE 42 7β-Phenoxyacetamido-6αH-8-oxo-4-thia-1-azabicyclo[4.2.0.]oct-2-ene-4-carboxylic acid To a cooled solution (0° C.) of 0.477 g (1 mmol) of trichloroethyl 7β-phenoxyacetamido-6αH-2-hydroxy-8-oxo-4-thia-1-azabicyclo[4.2.0.]octane-2-carboxylate in 10 ml ethyl acetate is added 65 μl of trifluoroacetic anhydride and then 362 μl of pyridine. The reaction is stirred overnight at room temperature and then diluted with ethyl acetate. The solution is washed with NaHCO3 solution, 3N HCl and saturated saline solution. The dried solution is evaporated to give the ester of the title product which is recrystallized from benzene; 157 mg (34%). In 24 ml solution of dimethylformamide-glacial acetic acid (1:1) is dissolved 70 mg of the above ester. To this solution is added over a 1.5 hour period 500 mg of zinc dust which has been treated with 5% HCl for 3 minutes, washed with water, ethanol, and ether and then dried. The reaction mixture is stirred 3 hours at room temperature, diluted with water, acidified with 3N HCl and extracted with ethyl acetate. The extracts are washed with a large volume of 5% NaHCO3. The aqueous solution is acidified to pH 2 with HCl and extracted with ethyl acetate. The dried extracts are concentrated in vacuo and then high vacuum is used to remove residual acetic acid. The residue is triturated with ether-hexane, dissolved in methylene chloride and precipitated with hexane to give the title product, mp 194°-5° (dec). | |
With pyridine; hydrogenchloride; sodium hydrogencarbonate; trifluoroacetic anhydride; zinc In dichloromethane; acetic acid; ethyl acetate | 42 7β-Phenoxyacetamido-6αH-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-4-carboxylic acid EXAMPLE 42 7β-Phenoxyacetamido-6αH-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-4-carboxylic acid To a cooled solution (0° C.) of 0.477 g (1 mmol) of trichloroethyl 7β-phenoxyacetamido-6αH-2-hydroxy-8-oxo-4-thia-1-azabicyclo[4.2.0]octane-2-carboxylate in 10 ml ethyl acetate is added 65 μl of trifluoroacetic anhydride and then 362 μl of pyridine. The reaction is stirred overnight at room temperature and then diluted with ethyl acetate. The solution is washed with NaHCO3 solution, 3 N HCl and saturated saline solution. The dried solution is evaporated to give the ester of the title product which is recrystallized from benzene; 157 mg (34%). In 24 ml solution of dimethylformamide-glacial acetic acid (1:1) is dissolved 70 mg of the above ester. To this solution is added over a 1.5 hour period 500 mg of zinc dust which has been treated with 5% HCl for 3 minutes, washed with water, ethanol, and ether and then dried. The reaction mixture is stirred 3 hours at room temperature, diluted with water, acidified with 3N HCl and extracted with ethyl acetate. The extracts are washed with a large volume of 5% NaHCO3. The aqueous solution is acidified to pH 2 with HCl and extracted with ethyl acetate. The dried extracts are concentrated in vacuo and then high vacuum is used to remove residual acetic acid. The residue is triturated with ether-hexane, dissolved in methylene chloride and precipitated with hexane to give the title product, mp 194°-5° (dec). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 14h; | 5.1.29. 1-Acetyl-N-{2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzyl}-3-phenyl-4-piperidinamine hydrochloride (36) General procedure: To a mixture of 32 (0.15 g, 0.30 mmol), acetic acid (0.022 g, 0.36 mmol), HOBt (0.055 g, 0.36 mmol) and Et3N (0.061 g, 0.60 mmol) in DMF (3 mL) was added WSC (0.069 g, 0.36 mmol). After stirring at room temperature for 14 h, the reaction mixture was poured into H2O and extracted with EtOAc. The extract was washed with aqueous NaHCO3 and brine, dried and concentrated. The residue was purified by preparative HPLC to give an oil, which was treated with 1 equiv of 4 N HCl-EtOAc to provide 36 (0.12 g, 78%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With lithium hydroxide monohydrate; water In tetrahydrofuran at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 17h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With triethylamine; sodium iodide In acetone at 70℃; for 16h; | 39 Example 39: 1- (2- (N-methylacetamido) acetoyloxy) ethyl (S) -1- (2-chlorophenyl) -2-oxocyclohexylmethylcarbamate (A-39) To a solution of compound 2 (50 mg, 0.15 mmol) , NaI (43 mg, 0.29 mmol) and 2- (N-methylacetamido) acetic acid (95 mg, 0.73 mmol) in acetone (2 mL) was added Et 3N (0.10 mL, 0.73 mmol) . The reaction was heated to 70 for 16 h. The reaction was concentrated and re-dissolved in DCM (5 mL) , washed with aqueous saturated NaHCO 3 solution (5 mL) and brine (5 mL) . The organic layer was dried over MgSO 4, filtered and concentrated to get an oil, which was purified on silica gel column eluting with hexane/EA (100%hexane to 1/4) to afford 36 mg (57%yield) of the titled compound (A-39) as a white foam. [0547] 1HNMR (600 MHz, DMSO-d 6) δ = 1.29-1.59 (m, 3H) , 1.59-1.78 (m, 3H) , 1.81-1.90 (m, 1H) , 1.94-2.07 (m, 3H) , 2.25-2.42 (m, 2H) , 2.53-2.68 (m, 1H) , 2.78 (s, 1H) , 2.92-3.03 (m, 5H) , 3.06-3.19 (m, 1H) , 3.99-4.29 (m, 2H) , 6.61-6.72 (m, 1H) , 6.91-7.02 (m, 1H) , 7.28-7.37 (m, 2H) , 7.43-7.50 (m, 1H) . [0548] MS (ESI) : [M + H] + = 439.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With potassium carbonate; sodium iodide In acetone at 70℃; for 1h; | 38 Example 38: (2- (N-methylacetamido) acetoyloxy) methyl (S) -1- (2-chlorophenyl) -2-oxocyclohexylmethylcarbamate (A-38) To a solution of compound 5 (50 mg, 0.15 mmol) , NaI (45 mg, 0.30 mmol) and 2- (N-methylacetamido) acetic acid (99 mg, 0.76 mmol) in acetone (2 mL) was added K 2CO 3 (105 mg, 0.76 mmol) . The reaction was heated to 70 for 1 h. The reaction was concentrated and re-dissolved in DCM (5 mL) , washed with aqueous saturated NaHCO 3 solution (5 mL) and brine (5 mL) . The organic layer was dried over MgSO 4, filtered and concentrated to get an oil, which was purified on silica gel column eluting with hexane/EA (100%hexane to 1/4) to afford 25 mg (39%yield) of the titled compound (A-38) as a white foam. [0542] 1HNMR (600 MHz, DMSO-d 6) δ = 1.61-1.76 (m, 3H) 1.89-2.01 (m, 2H) , 2.01-2.05 (m, 2H) , 2.30-2.40 (m, 2H) , 2.54-2.73 (m, 2H) , 2.80 (s, 1H) , 2.96 (s, 3H) , 3.03 (s, 2H) , 3.08-3.18 (m, 1H) , 4.06-4.37 (m, 2H) , 5.61-5.86 (m, 2H) , 6.93-7.00 (m, 1H) , 7.29-7.38 (m, 2H) , 7.43-7.50 (m, 1H) . [0543] MS (ESI) : [M + H] + = 425.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | Stage #1: N-acetylsarcosine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.166667h; Stage #2: C6H11NO3*ClH With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; |
Tags: 5888-91-5 synthesis path| 5888-91-5 SDS| 5888-91-5 COA| 5888-91-5 purity| 5888-91-5 application| 5888-91-5 NMR| 5888-91-5 COA| 5888-91-5 structure
[ 82505-42-8 ]
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P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
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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