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CAS No. : | 73259-81-1 | MDL No. : | MFCD00236843 |
Formula : | C8H16N2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KRJLRVZLNABMAT-YFKPBYRVSA-N |
M.W : | 204.22 | Pubchem ID : | 2755946 |
Synonyms : |
Boc-L-Dap-OH
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.75 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 49.56 |
TPSA : | 101.65 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) : | -9.43 cm/s |
Log Po/w (iLOGP) : | 1.51 |
Log Po/w (XLOGP3) : | -2.66 |
Log Po/w (WLOGP) : | -0.08 |
Log Po/w (MLOGP) : | -0.3 |
Log Po/w (SILICOS-IT) : | -0.93 |
Consensus Log Po/w : | -0.49 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 0.97 |
Solubility : | 1890.0 mg/ml ; 9.24 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 1.07 |
Solubility : | 2420.0 mg/ml ; 11.9 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -0.31 |
Solubility : | 101.0 mg/ml ; 0.494 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.68 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
99% | With potassium carbonate; In hexane; N,N-dimethyl-formamide; | Step 1 Preparation of (R)-(-)-2-tert-butoxycarbonylamino-3-(2-nitrophenylamino)propionic acid (R)-2-tert-Butoxycarbonylamino-3-aminopropionic acid (5 g) and potassium carbonate (6.77 g) were added to a solution of 2-fluoronitrobenzene (3.45 g) in N,N-dimethylformamide (60 ml), and the mixture was stirred overnight at 70 C. After the reaction mixture was allowed to cool, the reaction mixture was poured into ice-water and washed with ethyl acetate. The water layer was adjusted to pH 3 with 1N hydrochloric acid, extracted with ethyl acetate. This organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Hexane was added to the residue for crystallization, collected by filtration,to thereby obtain 7.9 g of the title compound (Yield 99%). [alpha] D25 (C=1.00, CHCl3): -145 |
95% | With potassium carbonate; In ethanol; for 4h;Reflux; | Step 1 - Boc D Diaminopropionic acid (3g) was dissolved in 100 ml of ethanol. Potassium carbonate (1.095 g) and 2-fluoronitrobenzene (1.71 ml) was added followed by refluxing for 4 hours. The reaction mixture was concentrated under pressure, water was added and the resulting mixture was washed with diethyl ether. 1 N HC1 was the added to the aqueous layer to adjust its pH to 3 followed by extraction with ethyl acetate. The organic layer was then dried over sodium sulfate and then the solvent was evaporated under reduced pressure, where 4.5g (95%) of the following compound was obtained as a bright orange solid. |
With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 70℃; for 36h; | EXAMPLE 1; rr^)-l-r(i?V5-Cvclopropylmethyl-2-oxo-l-r2.2.2-trifluoro-ethylV2.3.4.5-tetrahvdro-lH- benzo|'l[1.4]diazepin-3-ylcarbamoyll-2-('4-fluoro-phenyl)-ethyll-carbamic acid ter/-butyl ester; Step 1: Preparation of ((i?)-2-oxo-2,3,4,5-tetrahydro-lH-benzo[b][l,4]diazepin-3-yl)-carbamic acid tert-butyl ester:; A mixture of l-fluoro-2-nitrobenzene (7.77 g, 55.1 mmol), (i?)-3-amino-2-/ert- butoxycarbonylamino-propionic acid (9.98 g, 48.9 mmol) and sodium bicarbonate (13.34 g, 158.8 mmol) in N, N-dimethylformamide (50 mL) was heated at 70 OC for 36 hours. The reaction was then cooled to room temperature, diluted with ethyl acetate (200 mL) and washed three times with 1 : 1 saturated aqueous NH4CI solution:H2theta. The aqueous wash layers were combined and extracted with ethyl acetate (50 mL). The ethyl acetate extracts were combined, washed with saturated aqueous NaCl solution (50 mL), dried over MgStheta4, filtered and concentrated in vacuo to give an oil that was used without further purification in the next reaction described below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; N,O-Bis(trimethylsilyl)trifluoroacetamide; In N,N-dimethyl-formamide; at 0 - 20℃; for 1.5h; | A solution of <strong>[73259-81-1](R)-2-tert-butoxycarbonyl-3-aminopropionic acid</strong> (1.0 g) in pyridine (Smi) and DMF (5 ml) was treated with BSTFA (3.9 ml). After 30 in at rt the reaction was cooled to 0 C. and a solution of phenylmethanesulfonyl chloride (0.9 g) in DMF (2 ml) was added. After stirring for 1 h at rt the reaction mixture was partitioned between 1M aqueous citric acid and ethyl acetate. The organic layer was washed with water and brine, dried (MgSO4), and evaporated. Chromatography (silica gel, dichloromethane-methanol) gave the subtitle compound (0.5 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In 1,4-dioxane; water; at 20℃; for 24h; | To a solution of <strong>[73259-81-1](R)-2-tert-butoxycarbonyl-3-aminopropionic acid</strong> (2.0 g) in 1,4-dioxan (40 ml) and water (20 ml) was added triethylamine (6.9 ml) followed by toluene-4-sulfonyl chloride (2.2 g). The solution was then stirred at rt for 24 h, concentrated, and then partitioned between aqueous sodium hydrogen carbonate and ethyl acetate. The organic layer was dried (MgSO4) and evaporated to give the subtitle compound (2.4 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 80℃; | -amino-N-(tert-butoxycarbonyl)-D-alanine and potassium carbonate. The reaction liquid was stirred overnight at 800C. The reaction liquid was cooled to room temperature, followed by removing ethanol under reduced pressure and adding water to the residue. The resultant aqueous solution was washed with ether twice, and the aqueous phase was adjusted to pH 4.3 with IM hydrochloric acid.Two extractions were carried out with ethyl acetate, and the organic phase was washed with a saturated saline solution, dried over anhydrous sodium sulfate and thereafter concentrated under reduced pressure to yield the crude title compound as an orange solid. ESI-MS(m/e):344[M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at 20℃; | 110 mg of the material (2) shown in Table 2 was dissolved in 12 ml of dichloromethane (DCM) (Wako Pure Chemical). 80 mg of Boc-Dap-OH (Bachem) was added to the solution, and then 6 ml of triethylamine (TEA) (Wako Pure Chemical) was added little by little, followed by stirring at room temperature overnight. After the reaction was over, the reaction solution was subjected to evaporation by an evaporator to remove the solvent, supplied with 5% NaHCO3(aq), and further supplied with 0.3 N HCl until the solution got acidic to form a precipitate, which was then filtered by suction and dried in a desiccator. Boc-Dap-OH and the compound (3) thus obtained, 2-tert-butoxycarbonylamino-3-(10-methyl-9-oxo-9,10-dihydro-acridine-2-sulfonylamino)-propionic acid were analyzed to get their respective 1H-NMR data. The results are shown in FIG. 6 and FIG. 7. The product was further purified by silica gel column chromatography to give a substance, which was then analyzed to give the 1H-NMR data. The result was shown in FIG. 8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
146 mg | at 120℃; for 0.75h;Irradiation; | A microwave vessel was charged with norbornene anhydride (82 mg, 0.5 mmol) and N?(tertbutoxycarbonyl) di-1,2-aminopropinoic acid (Boc-Dap-OH) (102 mg, 0.5 mmol) and EtOAc (0.5 mL). The resulting mixture was heated to 120 C under microwave irradiation for 45 min. The solution was cooled, diluted with EtOAc (20 mL), washed with 1 M HCl (3 × 15 mL), dried with MgSO4, filtered and concentrated in vacuo to afford the title compound (146 mg, 83%) as a white solid Mp 165-170 C; deltaH (270 MHz, CDCl3) 1.43 (9H, s, t-Bu), 1.54 (1H, d, J 8.6, H10b), 1.73 (1H, d, J 8.9, H10a), 3.31 (2H, m, H1, H7), 3.38(2H, bs, H2, H6), 3.77 (2H, m, H1?), 4.39 (1H, m, H2?), 5.26 (1H, d, J 5.8, NH), 6.12 (2H, m, H8, H9); deltaC (75 MHz, CDCl3) 178.2, 177.6, 172.8, 155.7, 134.8, 134.2, 80.7, 77.2, 52.2, 52.0, 45.9, 45.0, 44.9, 38.8, 28.3; HRMS m/z (-ESI) 349.1442 ([C17H22N2O6-H]- requires 349.1400). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.58 g | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; | Fluorescently Labeled Amino Acids 16-24; General Procedure General procedure: The appropriate coumarin-3-carboxylic acid 8-12 (1.0 equiv) and Nhydroxysuccinimide(1.5 equiv) were dissolved in DMF (15-60 mL)and the solution was cooled to 0 °C. EDC·HCl (1.5 equiv) was addedand the mixture was stirred for 3 h. During this time, r.t. was reachedand the mixture was diluted with EtOAc (50-300 mL) and washedwith aq 10% citric acid (50-150 mL), aq sat. NaHCO3 (50-150 mL), andbrine (50-150 mL). The organic phase was dried (Na2SO4), filtered,and evaporated. The NHS-ester was dissolved in DMF (25-50 mL) andcooled to 0 °C. DIPEA (2.4 equiv) and Nα-Boc-L-Lys-OH (15) or compound 14 (1.2 equiv) were added and the solution was stirred at r.t.overnight. The mixture was diluted with EtOAc (50-300 mL) andwashed with aq 10% citric acid (3 × 50-150 mL) and brine (50-150mL), dried (Na2SO4), filtered, and evaporated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ca. 100% | L-glutamic acid di-tert-butyl ester hydrochloride 600 mg (2 mmol) and triethylamine 1 mL were dissolved in 20 mL anhydrous methylenechloride. The solution was cooled to -78 C. Triphosgene 200 mg (0.66 mmol) was dissolved in 3 mL anhydrous methylene chloride and added by drop. The reaction was slowly warmed up to room temperature and stirred for 30 mi (R)-3-amino-2-((tert- butoxycarbonyl)amino)propanoic acid 400 mg (2 mmol) and triethylamine 0.4 mL were added. The reaction was kept at room temperature for 24 h. The organic layerwas washed with 2N HC1 and dried with sodium sulfate. After the solvent was removed under vacuum, 1.0 g (R)-2-amino-3 -(3 -((S)-i ,5-di-tert-butoxy- 1,5- dioxopentan-2-yl)ureido)propanoic acid was obtained and used for the next steps without further purification. The yield was around 100%. (?H NMR (400 MHz, CDC13): oe 6.17-6.00(br, 3H). 4.31(m, 2H), 3.71-3.51(m, 2H), 2.37-2.32(m, 2H), 2.11-2.06(m, 1H), 1.91-1.80(m, 1H) 1.51-1.41(m, 27H). MS: 446 (M+H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | HADA/HALA: To a flame-dried flask, 7-hydroxycoumarin-3-carboxylic acid (HCC) was added in anhydrous DMF (14.5 mL, 0.1 M) under an atmosphere of argon. Carbonyldiimidazole (236 mg, 1.455 mmol) was added in one portion and stirred at room temperature (RT) for 2 hours. (0141) Boc-D-2,3-diaminopropionic acid (for HADA) or Boc-L-2,3-diaminopropionic acid (for HALA) (297 mg, 1.455 mmol) was added in one portion and the reaction mixture was allowed to stir at RT overnight (17 hours). The majority of the solvent was removed in vacuo, and the product was diluted with EtOAc (100 ml) and washed with 1 N HCl (50 ml) and water (100 ml). The water layers were combined and back-extracted with EtOAc (50 ml) to prevent loss of product due to an emulsion. The organic layers were combined, washed with brine (50 ml), dried over Na2SO4, filtered, and the solvent was removed in vacuo. Without further purification the crude product was treated with trifluoroacetic acid/dichloromethane (50:50, 10 ml) for 30 minutes at RT, and the solvent was removed in vacuo. The product was purified via reverse-phase HPLC with 10%-90% MeCN/H2O. The pure fractions were concentrated in vacuo, and the product was redissolved in 1 N HCl/MeCN and lyophilized to yield the desired product as a pale yellow solid (297 mg, 62% for HADA and 277 mg, 58% for HALA). [alpha]20D=-21.8 (c 2.2, DMSO-d6); HRMS-ESI-TOF m/z calc'd for C13H12O6N2 ([M+H]+): 293.0774. Found 293.0774; HPLC: tR=5.96 min (10-90% MeCN/H2O over 10 minutes); 1H NMR (400 MHz, DMSO-d6) delta=2.46 (s, 1H), 3.69-3.77 (m, 1H), 3.79-3.87 (m, 1H), 4.07 (t, J=5.6 Hz, 1H), 6.85 (d, J=2.0 Hz, 1H), 6.89 (dd, J=2.0, 8.4 Hz, 1H), 7.89 (d, J=8.8 Hz, 1H), 8.43 (br s, 3H), 8.76 (s, 1H), 8.86 (t, J=6.2 Hz, 1H), 11.34 (br s, 1H); 13C NMR (100 MHz, DMSO-d6): delta=52.1, 102.3, 111.3, 113.5, 115.0, 132.5, 148.8, 156.8, 161.2, 163.1, 164.6, 169.7; the signal for one carbon was overlapping with the solvent peak. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | NADA/NALA: Boc-D-2,3-diaminopropionic acid (for NADA) or Boc-L-2,3-diaminopropionic acid (for NALA) (100 mg, 0.49 mmol) and sodium bicarbonate (123 mg, 1.47 mmol) were dissolved in water (1.8 ml) and heated to 55 C. in water bath. A solution of 4-chloro-7-nitrobenzofurazan (NBD, 108 mg, 0.539 mmol) in methanol (8.5 ml) was added dropwise over 10 minutes. Care was taken at all times to avoid excessive exposure to light during the reaction and workup. The reaction was allowed to stir at 55 C. for 1 hour. The solvent was removed in vacuo and acidified with 1 N HCl. The aqueous mixture was extracted with dichloromethane (50 ml per extraction×3 extractions) and the organic extracts were washed with brine (50 ml), dried over Na2SO4, filtered, and the solvent was removed in vacuo. Without further purification the crude product was treated with 4 N HCl/dioxane (10 ml) for 1 hour at RT, and the solvent was removed in vacuo. The product was purified via reverse-phase HPLC with 20%-90% MeCN/H2O. The pure fractions were concentrated in vacuo, and the product was redissolved in 1 N HCl/MeCN and lyophilized to yield the desired product as a bright orange solid (105 mg, 71% for both NADA and NALA). [alpha]20D=-32 (c 1.1, DMSO-d6) HRMS-ESI-TOF m/z calc'd for C9H9O5N5 ([M+H]+): 268.0682. Found 268.0680; HPLC: tR=5.02 minutes (20-90% MeCN/H2O over 10 minutes). 1H NMR (400 MHz, DMSO-d6): delta=4.06 (m, 2H), 4.29 (m, 1H), 6.61 (d, J=8.0 Hz, 1H), 8.56 (d, J=8.0 Hz, 1H), 8.66 (br s, 3H), 9.32 (br s, 1H); 13C NMR (100 MHz, DMSO-d6): delta=43.4, 51.5, 100.5, 122.5, 138.1, 144.4, 144.9, 145.2, 169.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
930 g | In a 50L reactor, 6.5 L of 50% aqueous methanol solution, 1.346 kg of N-alpha-Boc-D-alpha, beta-diaminopropionic acid were added, and the mixture was cooled to 0-5 C, and 332 g of lithium hydroxide monohydrate was added in portions. The pH was measured at about 8 and stirred for 40 minutes. 1.03 kg of potassium oxalate monomethyl salt was dissolved in 7715 mL of a 50% aqueous methanol solution, and added dropwise to the above reaction solution, maintaining 0-5 C during the process. After the completion of the dropwise addition, the temperature was raised to room temperature for 20 hours. After suction filtration, the filter cake was washed once with 2.5 L of a 50% aqueous methanol solution and 2.5 L of acetone, and dried to give a white solid. The solid was added to 5850 mL of water, and the temperature was lowered to below 10 C, and 2N hydrochloric acid was added dropwise.Adjust the pH to 2.1-2.2 and control the temperature to 0-10 C during the process. After the completion of the dropwise addition, stirring was carried out for 2-3 hours at room temperature, and stirring was continued for 4-6 hours at a temperature of 0-10. After suction filtration, the filter cake was added to ice water, stirred for 2 hours, and the filter cake was washed twice with 2.5 L of ice water, 2.5 L of methanol, 2.5 L of acetone, and thoroughly dried to obtain a white solid 930 g.The purity is 99.5%, and the external standard method is 99%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
400 g | With hydrazine hydrate; at 80℃; for 6h; | 500 g of Boc-D-serine mesylate was dissolved in 1 L of DMSO, 390 g of potassium phthalimide was added, 198 g of potassium hydroxide was added, and the mixture was stirred at 30 degrees for 12 hours. After the reaction was completed, the solution was filtered, and the filtrate was added to 200 g of 80%. Hydrazine hydrate, heated to 80 C for 6 hours, cooled to 0 C, added 4N hydrochloric acid to adjust the pH to 6-7, precipitate a large amount of white solid, suction filtration, filter cake collected and beat with 95% ethanol 0 degree for 2 hours It was suction filtered and dried to give a white solid (400 g). |
[ 77215-54-4 ]
(S)-tert-Butyl 3-amino-2-((tert-butoxycarbonyl)amino)propanoate
Similarity: 0.93
[ 181228-33-1 ]
(S)-Methyl 3-amino-2-((tert-butoxycarbonyl)amino)propanoate hydrochloride
Similarity: 0.93
[ 75638-15-2 ]
(R)-2-((tert-Butoxycarbonyl)amino)propanoic acid hydrate
Similarity: 0.88
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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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