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CAS No. : | 614-19-7 | MDL No. : | MFCD00008064 |
Formula : | C9H11NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UJOYFRCOTPUKAK-UHFFFAOYSA-N |
M.W : | 165.19 | Pubchem ID : | 69189 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 45.5 |
TPSA : | 63.32 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) : | -8.3 cm/s |
Log Po/w (iLOGP) : | 1.05 |
Log Po/w (XLOGP3) : | -1.4 |
Log Po/w (WLOGP) : | 0.84 |
Log Po/w (MLOGP) : | 1.1 |
Log Po/w (SILICOS-IT) : | 0.86 |
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) : | -0.15 |
Solubility : | 116.0 mg/ml ; 0.701 mol/l |
Class : | Very soluble |
Log S (Ali) : | 0.57 |
Solubility : | 616.0 mg/ml ; 3.73 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -1.86 |
Solubility : | 2.3 mg/ml ; 0.0139 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.41 |
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: |
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* 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 |
---|---|---|
c) Deacylation of (S)-3-glutarylamide-3-phenylpropanoic acid by basic hydrolysis 557.2 g of a mixture of (S)-3-glutarylamide-3-phenylpropanoic acid and (R)-3-glutarylamide-3-phenylpropanoic acid in a 90:10 ratio, obtained in preceding step b), were distilled in 3.91 liters of distilled water and 1.65 liters of 30percent (weight/volume) sodium hydroxide. The reaction mixture was stirred at 70° C. for 4 days. The reaction mixture was then cooled to 15° C. The product obtained was precipitated with adjustment of the pH to 6.9 by addition of 3.21 liters of 37percent (weight/volume) hydrochloric acid, filtered off, and dried to constant weight under vacuum at 45° C. This gave 202.4 g of (S)-3-amino-3-phenylpropanoic acid and (R)-3-amino-3-phenylpropanoic acid with an enantiomeric excess of greater than 98percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With amano-lipase PS, from Burkholderia cepacia; In aq. phosphate buffer; tert-butyl methyl ether; at 50℃; for 25h;pH 7;Enzymatic reaction; | To 115 mL of a 50 mM aqueous solution of disodium hydrogen phosphate dodecahydrate with a pH of 7.00 was added 2.30 g of lipase (Amano Lipase PS; available from Aldrich) and stirred for 1 h at 50 °C. The clear solution was poured into a solution of ester rac-12 (46.25 g, 0.22 mol) in methyl tert-butyl ether (115 mL) and stirred for 24 h at 50 °C. After cooling to room temperature 190 mL acetone was added and the reaction mixture was stirred for 1 h at 0 °C. The resulting precipitate was filtered off and dried in vacuo to give 13 as a colourless solid (16.30 g, 0.10 mol, 45percent, 90percent based on S-12). [alpha]D20= -8.00 ° (c: 0.03, H2O), Lit.: [alpha]D25= -8 ° (H2O) [1]. Rf= 0.33(MeOH/CH2Cl22:1). 1H-NMR and 13C-NMR were identical to the spectra of rac-12. MS (ESI): m/z (percent) = 166.0 (100) [M + H+]. HRMS (MALDI): calcd. for C9H12NO2 [M + H+]: 166.08626; found 166.08619. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Into the 250 ml reaction flask added racemic 3-amino-3-phenylpropionic acid: water, acetic acid, ethanol, camphorsulfonic acid, then heated to 50-80°C, and reacted for 10 minutes. The reaction was cool to 5-20°C and the chiral inducing reagent was added to crystallize, and were filtered to give the S-type optical isomer 3-amino-3-phenylpropionic acid camphorsulfonic acid double salt.The molar ratio of the chiral reagent and the racemate is 0.5 ~ 1.5: 1. The chiral induction agent is camphorsulfonic acid *o-chlorophenylate (or o-chlorophenyl Glycine salt). The molar ratio of the chiral inducing agent to the racemic body is 0.001 to 0.005:1. The S-type optical isomer 3 amino-3-phenylpropionic acid camphorsulfonic acid double salt was added, and the pH was adjusted to 7-8 with a 10percent mass aqueous ammonia solution under stirring, and left to cool at 10°C for5 Hour, filtered to obtain S-type optical isomer 3-amino-3-phenylpropionic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With sodium hydrogencarbonate; at 20℃; for 24h; | (S)-3-Amino 3-phenylpropionic acid (0.33 g, 2 mmol)Dissolved in 3 mL of saturated NaHCO3,Di-tert-butyl carbonate (0.52 g, 2.2 mmol) was added slowly.Room temperature reaction for 24 hours.Then add 1N hydrochloric acid solution to adjust PH 2-3,The aqueous phase is extracted three times with ethyl acetate and the organic layers are combined.After washing the organic layer with saturated sodium chloride solution,After drying over anhydrous magnesium sulfate,Evaporation gave (S)-3-tert-butoxycarbonylamino-3-phenylpropionic acid 0.52 g (98percent). |
0.2877 g | With sodium hydrogencarbonate; In tetrahydrofuran; water; at 0 - 20℃; for 10h; | (S)-3-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid: <strong>[614-19-7](S)-3-amino-3-phenylpropanoic acid</strong> (0.200 g, 1.21 mmol) was dissolved in THF (3.0 ml) and Water (3.0 ml) and the resulting white mixture was cooled to 0° C. Finely powdered NaHCO3 (0.305 g, 3.63 mmol) was added in one portion, followed by Boc2O (0.317 g, 1.45 mmol). The reaction was stirred overnight for 10 hours while it gradually warmed to room temperature. The reaction was washed with diethyl ether (2×10 mL). The remaining aqueous layer was carefully acidified to pH 4 with saturated citric acid solution (aqueous). The solution turned clear before a white solid eventually precipitated. After extraction with dichloromethane (4×10 mL), the extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give the product as a white solid (0.2877 g). This material was used without further purification |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium dihydrogenphosphate; water;Amano Lipase PS; at 30℃; for 15.5h;pH 8.2;Resolution of racemate;Product distribution / selectivity; | To 1.5 mL of 50 mmol/L aqueous potassium phosphate solution with a pH of 8.2 was added 300 mg (1.67 mmol) of methyl 3-amino-3-phenylpropionate (racemic mixtures) and the mixture was maintained to 30°C. To the obtained mixture was added 15 mg of lipase (Amano Lipase PS (trade name); available from Aldrich Corporation) originated from Burkholderia cepacia (Pseudomonas cepacia) at the same temperature, and the mixture was reacted while stirring at 30°C. After 15 hours, 0.5 mL of acetone was added to the reaction mixture and the resulting mixture was filtered to give 96.8 mg of (S)-3-amino-3-phenylpropionic acid (isolation yield based on methyl 3-amino-3-phenylpropionate (racemic mixtures)=35.0percent) and 10 mg of an enzyme fixing agent as a mixture. The (S)-3-amino-3-phenylpropionic acid was led to an n-propyl ester according to the conventional manner, and when an optical purity thereof was measured by using high performance liquid chromatography which uses an optically active column, it was 49.9percent ee. When an optical purity of the (R)-methyl 3-amino-3-phenylpropionate was measured by using high performance liquid chromatography which uses an optically active column, it was 46.8percent ee. Incidentally, the E value in the present reaction was 4. Analytical conditions of high performance liquid chromatography; Optically active methyl 3-amino-3-phenylpropionate Column: Chiral CD-Ph (0.46cmPhix25cm, available from Shiseido Co., Ltd.) Solvent: acetonitrile/water (=1/9 (volume ratio)) Potassium dihydrogen phosphate 40 mmol/L Adjusted to pH 3.5 with phosphoric acid Flow rate: 0.5 mL/min Temperatrure: 30°C Wavelength: 220 nm Also, physical properties of the (S)-3-amino-3-phenylpropionic acid were the same as those shown in Example 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Product distribution / selectivity; | Example 1 (Syntheses of (S)-3-amino-3-phenylpropionic acid and (R)-n-propyl 3-amino-3-phenylpropionate) To a mixed solution comprising 4.75 mL of 50 mmol/L aqueous potassium phosphate solution with a pH of 8.2 and 0.25 mL of t-butyl methyl ether was added 1.00 g (4.82 mmol) of n-propyl 3-amino-3-phenylpropionate (racemic mixtures) synthesized in Reference example 2 and the mixture was maintained to 30°C. To the obtained mixture was added 50 mg of lipase (Amano Lipase PS (trade name); available from Aldrich Corporation) originated from Burkholderia cepacia (Pseudomonas cepacia) at the same temperature, and the mixture was reacted while stirring at 30°C. After 15 hours, 3 mL of acetone was added to the reaction mixture and the resulting mixture was filtered to give 359 mg of (S)-3-amino-3-phenylpropionic acid (isolation yield based on n-propyl 3-amino-3-phenylpropionate (racemic mixtures)=44.0percent) and 37 mg of an enzyme fixing agent as a mixture. The (S)-3-amino-3-phenylpropionic acid was led to an n-propyl ester according to the conventional manner, and when an optical purity thereof was measured by using high performance liquid chromatography which uses an optically active column, it was 99.9percent ee. When an optical purity of the (R)-n-propyl 3-amino-3-phenylpropionate was measured by using high performance liquid chromatography which uses an optically active column, it was 99.9percent ee. Incidentally, the E value in the present reaction was larger than 10000. Analytical conditions of high performance liquid chromatography; Optically active n-propyl 3-amino-3-phenylpropioriate Column: Chiral CD-Ph (0.46cmPhix25cm, available from Shiseido Co., Ltd.) Solvent: acetonitrile/water (=1/9 (volume ratio)) Potassium dihydrogen phosphate 40mM Adjusted to pH 3.5 with phosphoric acid Flow rate: 1.0 mL /min Temperatrure: 30°C Wavelength: 220 nm Also, physical properties of the (S)-3-amino-3-phenylpropionic acid were as follows. 1H-NMR (delta (ppm), D2O+DCl) : 3.06 (dd, 1H, J=17.1, 6.8Hz), 3.17 (dd, 1H, J=17.1, 7.3Hz), 4.76 (dd, 1H, J=7.3, 6.8Hz), 3.77 (s, 2H), 7.45 (m, 5H) 13C-NMR (delta (ppm), D2O+DCl) : 40.5, 54.4, 130.0, 132.3, 132. 6, 138.0, 176.3 MS (EI) m/z: 165 (M+) MS (CI, i-C4H10) m/z: 166 (MH+) Elemental analysis; Calcd: C, 65.44percent; H, 6.71percent; N, 8.48percent Found: C, 65.18percent; H, 6.78percent; N, 8.34percent. Physical properties of (R)-n-propyl 3-amino-3-phenylpropionate were as follows. 1H-NMR (delta (ppm), CDCl3): 0.90 (d, 3H, J=7.3Hz), 1.55-1.65 (tq, 2H, J=7.3, 6.8Hz), 2.63 (d, 2H, J=6.8Hz), 4.01 (t, 2H, J=6.8Hz), 4.39 (d, 1H, J=6.8Hz), 7.20-7.35 (m, 5H) 13C-NMR (delta (ppm), CDCl3): 10.4, 21.9, 44.2, 52.7, 66.1, 126.2, 127.3, 128.6, 144.7, 172.0 MS (EI) m/z: 207 (M+) MS (CI, i-C4H10) m/z: 208 (MH+) Elemental analysis; Calcd: C,69.54percent; H,8.27percent; N,6.76percent Found: C,68.86percent; H,8.22percent; N,6.60percent; Example 2 (Syntheses of (S)-3-amino-3-phenylpropionic acid and (R)-n-propyl 3-amino-3-phenylpropionate) To a mixed solution comprising 4.75 mL of 50 mmol/L aqueous ammonium acetate solution with a pH of 8.3 and 0.25 mL of t-butyl methyl ether was added 1.00 g (4.82 mmol) of n-propyl 3-amino-3-phenylpropionate (racemic mixtures) synthesized in Reference example 2, and the mixture was maintained to 30°C. To the obtained mixture was added 50 mg of lipase (Amano Lipase PS (trade name); available from Aldrich Corporation) originated from Burkholderia cepacia (Pseudomonas cepacia) at the same temperature, and the mixture was reacted while stirring at 30°C. After 15 hours, 3 mL of acetone was added to the reaction mixture and the resulting mixture was filtered to give 359 mg of (S)-3-amino-3-phenylpropionic acid (isolation yield based on n-propyl 3-amino-3-phenylpropionate (racemic mixtures)= 44.0percent) and 38 mg of an enzyme fixing agent as a mixture. The (S)-3-amino-3-phenylpropionic acid was led to an n-propyl ester according to the conventional manner, and when an optical purity thereof was measured by using high performance liquid chromatography which uses an optically active column, it was 99.8percent ee. When an optical purity of the (R)-n-propyl 3-amino-3-phenylpropionate was measured by using high performance liquid chromatography which uses an optically active column, it was 79.4percent ee. Incidentally, the E value in the present reaction was 1945. Analytical conditions of high performance liquid chromatography; Optically active n-propyl 3-amino-3-phenylpropionate Column: Chiral CD-Ph (0.46cmPhi.x.25cm, available from Shiseido Co., Ltd.) Solvent: acetonitrile/water (=1/9 (volume ratio)) Potassium dihydrogen phosphate 40mM Adjusted to pH 3.5 with phosphoric acid Flow rate: 1.0 mL/min Temperatrure: 30°C Wavelength: 220 nm Also, physical properties of (S)-3-amino-3-phenylpropionic acid and (R)-n-propyl 3-amino-3-phenylpropionate were the same as those shown in Example 1.; Example 3 (Syntheses of (S)-3-amino-3-phenylpropionic acid and (R)-n-propyl 3-amino-3-phenylpr... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.9%; 45% | With potassium dihydrogenphosphate; water;Amano Lipase PS; In cyclohexane; at 30℃; for 17h;pH 8.2;Resolution of racemate;Product distribution / selectivity; | To 1.5 mL of 50 mmol/L aqueous potassium phosphate solution with a pH of 8.2 was added 300 mg (1.45 mmol) of n-propyl 3-amino-3-phenylpropionate (racemic mixtures) synthesized in Reference example 2 and the mixture was maintained to 30°C. To the obtained mixture was added 15 mg of lipase (Amano Lipase PS (trade name); available from Aldrich Corporation) originated from Burkholderia cepacia (Pseudomonas cepacia) at the same temperature, and the mixture was reacted while stirring at 30°C. After 17 hours, 1.0 mL of acetone was added to the reaction mixture and the resulting mixture was filtered to give 108 mg of (S)-3-amino-3-phenylpropionic acid (isolation yield based on n-propyl 3-amino-3-phenylpropionate (racemic mixtures)= 45.0percent) and 12 mg of an enzyme fixing agent as a mixture. The (S)-3-amino-3-phenylpropionic acid was led to an n-propyl ester according to the conventional manner, and when an optical purity thereof was measured by using high performance liquid chromatography which uses an optically active column, it was 99.3percent ee. When an optical purity of the (R)-n-propyl 3-amino-3-phenylpropionate was measured by using high performance liquid chromatography which uses an optically active column, it was 99.9percent ee. Incidentally, the E value in the present reaction was 1687. Analytical conditions of high performance liquid chromatography; Optically active n-propyl 3-amino-3-phenylpropionate Column: Chiral CD-Ph (0.46cmPhix25cm, available from Shiseido Co., Ltd.) Solvent: acetonitrile/water (=1/9 (volume ratio)) Potassium dihydrogen phosphate 40 mmol/L Adjusted to pH 3.5 with phosphoric acid Flow rate: 1.0 mL/min Temperatrure: 30°C Wavelength: 220 nm Also, physical properties of the (S)-3-amino-3-phenylpropionic acid and (R)-n-propyl 3-amino-3-phenylpropionate were the same as those shown in Example 1. Incidentally, determination of the absolute configuration of the optically active 3-amino-3-phenylpropionic acid was carried out as follows. A sign of specific rotation ([alpha]25D -7.96° (c 1.0, H2O)) of the optically active 3-amino-3-phenylpropionic acid obtained in Comparative example 1 and a sigh of specific rotation of (S)-3-amino-3-phenylpropionic acid described in Tetrahedron Asymmetry, 6 (7), 1601 (1995) (literature value [alpha]20D -6.42°(c 1.0, H2O)) are compared to each other to determine the absolute configuration. |
46%; 43% | With potassium dihydrogenphosphate; water;Amano Lipase PS; In cyclohexane; at 20 - 30℃; for 20.5h;pH 8.2;Resolution of racemate;Product distribution / selectivity; | To 1.25 mL of 50 mmol/L aqueous potassium phosphate solution with a pH of 8.2 was added 25 mg of lipase (Amano Lipase PS (trade name); available from Aldrich Corporation) originated from Burkholderia cepacia (Pseudomonas cepacia) and the mixture was stirred at room temperature for 30 minutes. The mixture was filtered, 1.25 mL of cyclohexane and 500 mg (2.41 mmol) of n-propyl 3-amino-3-phenylpropionate (racemic mixtures) synthesized in Reference example 2 were added to the resulting filtrate, and the mixture was reacted at 30°C under stirring. After 20 hours, 1.5 mL of acetone was added to the reaction mixture and the resulting mixture was stirred at 0°C for 1 hour. The reaction mixture was filtered to give 156 mg of (S)-3-amino-3-phenylpropionic acid (isolation yield based on n-propyl 3-amino-3-phenylpropionate (racemic mixtures)=43.0percent). Then, after the filtrate was concentrated under reduced pressure, 2.5 mL of ethyl acetate was added to the residue to extract the organic layer, and the organic layer was dried over anhydrous magnesium sulfate. After filtration, the fitrate was concentrated under reduced pressure to give 230 mg of (R)-n-propyl 3-amino-3-phenylpropionate (isolation yield based on n-propyl 3-amino-3-phenylpropionate (racemic mixtures)=46.0percent). (S)-3-amino-3-phenylpropionic acid was led to an n-propyl ester according to the conventional manner, and when an optical purity thereof was measured by using high performance liquid chromatography which uses an optically active column, it was 99.7percent ee. When an optical purity of the (R)-n-propyl 3-amino-3-phenylpropionate was measured by using high performance liquid chromatography which uses an optically active column, it was 97.3percent ee. Incidentally, the E value in the present reaction was 3037. Analytical conditions of high performance liquid chromatography; Optically active n-propyl 3-amino-3-phenylpropionate Column: Chiral CD-Ph (0.46cmPhix25cm, available from Shiseido Co., Ltd.) Solvent: acetonitrile/water (=1/9 (volume ratio)) Potassium dihydrogen phosphate 40mM Adjusted to pH 3.5 with phosphoric acid Flow rate: 1.0 mL/min Temperatrure: 30°C Wavelength: 220 nm Also, physical properties of the (S)-3-amino-3-phenylpropionic acid and (R)-n-propyl 3-amino-3-phenylpropionate were the same as those shown in Example 1. |
44% | With potassium dihydrogenphosphate; water;Amano Lipase PS; In tert-butyl methyl ether; at 30℃; for 15h;pH 8.2;Resolution of racemate;Product distribution / selectivity; | To a mixed solution comprising 4.75 mL of 50 mmol/L aqueous potassium phosphate solution with a pH of 8.2 and 0.25 mL of t-butyl methyl ether was added 1.00 g (4.82 mmol) of n-propyl 3-amino-3-phenylpropionate (racemic mixtures) synthesized in Reference example 2 and the mixture was maintained to 30°C. To the obtained mixture was added 50 mg of lipase (Amano Lipase PS (trade name); available from Aldrich Corporation) originated from Burkholderia cepacia (Pseudomonas cepacia) at the same temperature, and the mixture was reacted while stirring at 30°C. After 15 hours, 3 mL of acetone was added to the reaction mixture and the resulting mixture was filtered to give 359 mg of (S)-3-amino-3-phenylpropionic acid (isolation yield based on n-propyl 3-amino-3-phenylpropionate (racemic mixtures)=44.0percent) and 37 mg of an enzyme fixing agent as a mixture. The (S)-3-amino-3-phenylpropionic acid was led to an n-propyl ester according to the conventional manner, and when an optical purity thereof was measured by using high performance liquid chromatography which uses an optically active column, it was 99.9percent ee. When an optical purity of the (R)-n-propyl 3-amino-3-phenylpropionate was measured by using high performance liquid chromatography which uses an optically active column, it was 99.9percent ee. Incidentally, the E value in the present reaction was larger than 10000. Analytical conditions of high performance liquid chromatography; Optically active n-propyl 3-amino-3-phenylpropioriate Column: Chiral CD-Ph (0.46cmPhix25cm, available from Shiseido Co., Ltd.) Solvent: acetonitrile/water (=1/9 (volume ratio)) Potassium dihydrogen phosphate 40mM Adjusted to pH 3.5 with phosphoric acid Flow rate: 1.0 mL /min Temperatrure: 30°C Wavelength: 220 nm Also, physical properties of the (S)-3-amino-3-phenylpropionic acid were as follows. 1H-NMR (delta (ppm), D2O+DCl) : 3.06 (dd, 1H, J=17.1, 6.8Hz), 3.17 (dd, 1H, J=17.1, 7.3Hz), 4.76 (dd, 1H, J=7.3, 6.8Hz), 3.77 (s, 2H), 7.45 (m, 5H) 13C-NMR (delta (ppm), D2O+DCl) : 40.5, 54.4, 130.0, 132.3, 132. 6, 138.0, 176.3 MS (EI) m/z: 165 (M+) MS (CI, i-C4H10) m/z: 166 (MH+) Elemental analysis; Calcd: C, 65.44percent; H, 6.71percent; N, 8.48percent Found: C, 65.18percent; H, 6.78percent; N, 8.34percent. Physical properties of (R)-n-propyl 3-amino-3-phenylpropionate were as follows. 1H-NMR (delta (ppm), CDCl3): 0.90 (d, 3H, J=7.3Hz), 1.55-1.65 (tq, 2H, J=7.3, 6.8Hz), 2.63 (d, 2H, J=6.8Hz), 4.01 (t, 2H, J=6.8Hz), 4.39 (d, 1H, J=6.8Hz), 7.20-7.35 (m, 5H) 13C-NMR (delta (ppm), CDCl3): 10.4, 21.9, 44.2, 52.7, 66.1, 126.2, 127.3, 128.6, 144.7, 172.0 MS (EI) m/z: 207 (M+) MS (CI, i-C4H10) m/z: 208 (MH+) Elemental analysis; Calcd: C,69.54percent; H,8.27percent; N,6.76percent Found: C,68.86percent; H,8.22percent; N,6.60percent |
44% | With potassium dihydrogenphosphate; water;Amano Lipase PS; In toluene; at 20 - 30℃; for 18.5h;pH 8.2;Resolution of racemate;Product distribution / selectivity; | To 4.75 mL of 50 mmol/L aqueous potassium phosphate solution with a pH of 8.2 was added 50 mg of lipase (Amano Lipase PS (trade name); available from Aldrich Corporation) originated from Burkholderia cepacia (Pseudomonas cepacia) and the mixture was stirred at room temperature for 30 minutes. The mixture was filtered, and to the resulting filtrate were added 0.25 mL of toluene and 1.00 g (4.82 mmol) of n-propyl 3-amino-3-phenylpropionate (racemic mixtures) synthesized in Reference example 2, and the mixture was reacted at 30°C under stirring. After 18 hours, 3 mL of acetone was added to the reaction mixture and the resulting mixture was filtered to give 359 mg of (S)-3-amino-3-phenylpropionic acid (isolation yield based on n-propyl 3-amino-3-phenylpropionate (racemic mixtures)= 44.0percent) and 38 mg of an enzyme fixing agent as a mixture. The (S)-3-amino-3-phenylpropionic acid was led to an n-propyl ester according to the conventional manner, and when an optical purity thereof was measured by using high performance liquid chromatography which uses an optically active column, it was 99.5percent ee. When an optical purity of the (R)-n-propyl 3-amino-3-phenylpropionate was measured by using high performance liquid chromatography which uses an optically active column, it was 99.9percent ee. Incidentally, the E value in the present reaction was 4038. Analytical conditions of high performance liquid chromatography; Optically active n-propyl 3-amino-3-phenylpropionate Column: Chiral CD-Ph (0.46cmPhix25cm, available from Shiseido Co., Ltd.) Solvent: acetonitrile/water (=1/9 (volume ratio)) Potassium dihydrogen phosphate 40 mM Adjusted to pH 3.5 with phosphoric acid Flow rate: 1.0 mL/min Temperatrure: 30°C Wavelength: 220 nm Also, physical properties of (S)-3-amino-3-phenylpropionic acid and (R)-n-propyl 3-amino-3-phenylpropionate were the same as those shown in Example 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With ammonium acetate; water;Amano Lipase PS; In tert-butyl methyl ether; at 30℃; for 15h;pH 8.3;Resolution of racemate;Product distribution / selectivity; | To a mixed solution comprising 4.75 mL of 50 mmol/L aqueous ammonium acetate solution with a pH of 8.3 and 0.25 mL of t-butyl methyl ether was added 1.00 g (4.82 mmol) of n-propyl 3-amino-3-phenylpropionate (racemic mixtures) synthesized in Reference example 2, and the mixture was maintained to 30°C. To the obtained mixture was added 50 mg of lipase (Amano Lipase PS (trade name); available from Aldrich Corporation) originated from Burkholderia cepacia (Pseudomonas cepacia) at the same temperature, and the mixture was reacted while stirring at 30°C. After 15 hours, 3 mL of acetone was added to the reaction mixture and the resulting mixture was filtered to give 359 mg of (S)-3-amino-3-phenylpropionic acid (isolation yield based on n-propyl 3-amino-3-phenylpropionate (racemic mixtures)= 44.0percent) and 38 mg of an enzyme fixing agent as a mixture. The (S)-3-amino-3-phenylpropionic acid was led to an n-propyl ester according to the conventional manner, and when an optical purity thereof was measured by using high performance liquid chromatography which uses an optically active column, it was 99.8percent ee. When an optical purity of the (R)-n-propyl 3-amino-3-phenylpropionate was measured by using high performance liquid chromatography which uses an optically active column, it was 79.4percent ee. Incidentally, the E value in the present reaction was 1945. Analytical conditions of high performance liquid chromatography; Optically active n-propyl 3-amino-3-phenylpropionate Column: Chiral CD-Ph (0.46cmPhi.x.25cm, available from Shiseido Co., Ltd.) Solvent: acetonitrile/water (=1/9 (volume ratio)) Potassium dihydrogen phosphate 40mM Adjusted to pH 3.5 with phosphoric acid Flow rate: 1.0 mL/min Temperatrure: 30°C Wavelength: 220 nm Also, physical properties of (S)-3-amino-3-phenylpropionic acid and (R)-n-propyl 3-amino-3-phenylpropionate were the same as those shown in Example 1. |
With potassium hydroxide; water;Amano Lipase PS; In cyclohexane; at 30℃; for 26h;pH 8.2;Resolution of racemate;Product distribution / selectivity; | To a mixture comprising 500 mg (2.41 mmol) of n-propyl 3-amino-3-phenylpropionate (racemic mixtures) synthesized in Reference example 2 and 1.25 mL of cyclohexane was added 1.25 mL of water a pH of which had been adjusted to 8.2 with 1 mol/L aqueous potassium hydroxide solution, and the mixture was maintained to 30°C. To the obtained mixture was added 25 mg of lipase (Amano Lipase PS (trade name); available from Aldrich Corporation) originated from Burkholderia cepacia (Pseudomonas cepacia) at the same temperature, and the mixture was reacted while stirring at 30°C. After 26 hours, a reaction conversion reached 42.6percent. The (R)-n-propyl 3-amino-3-phenylpropionate was led to (R)-n-propyl 3-(2-furoylamino)-3-phenylpropionate, and when an optical purity thereof was measured by using high performance liquid chromatography which uses an optically active column, it was 73.4percent ee. Incidentally, the E value in the present reaction was 441. Analytical conditions of high performance liquid chromatography: optically active 3-(2-furoylamino)-3-phenylpropionic acid n-propyl ester Column: Chiralcel OJ-H (0.46cmPhix25cm, available from DAICEL CHEMICAL INDUSTRIES, LTD.) Solvent: hexane/isopropyl alcohol (=1/9 (volume ratio)) Flow rate: 0.5 mL/min Temperatrure: 30°C Wavelength: 220 nm Also, physical properties of the (S)-3-amino-3-phenylpropionic acid and (R)-n-propyl 3-amino-3-phenylpropionate were the same as those shown in Example 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium dihydrogenphosphate; water;Amano Lipase PS; In cyclohexane; at 30℃; for 59h;pH 8.2;Resolution of racemate;Product distribution / selectivity; | To a mixture comprising 500 mg (2.26 mmol) of n-butyl 3-amino-3-phenylpropionate (racemic mixtures) synthesized in Reference example 3 and 1.25 mL of cyclohexane was added 1.25 mL of 50 mmol/L aqueous potassium phosphate solution with a pH of 8.2 and the mixture was maintained to 30°C. To the obtained mixture was added 25 mg of lipase (Amano Lipase PS (trade name); available from Aldrich Corporation) originated from Burkholderia cepacia (Pseudomonas cepacia) at the same temperature, and the mixture was reacted while stirring at 30°C. After 59 hours, a reaction conversion reached 45.4percent. The n-Butyl (R)-3-amino-3-phenylpropionate was led to (R)-n-butyl 3-(2-furoylamino)-3-phenylpropionate, and when an optical purity thereof was measured by using high performance liquid chromatography which uses an optically active column, it was 82.2percent ee. Incidentally, the E value in the present reaction was 513. Optically active n-butyl 3-(2-furoylamino)-3-phenylpropionate Column: Chiralcel OJ-H (0.46cmPhix25cm, available from DAICEL CHEMICAL INDUSTRIES, LTD.) Solvent: hexane/isopropyl alcohol (=1/9 (volume ratio)) Flow rate: 0.5 mL/min Temperatrure: 30°C Wavelength: 220 nm Also, physical properties of the (S)-3-amino-3-phenylpropionic acid were the same as those shown in Example 1. Physical properties of the (R)-n-butyl 3-amino-3-phenylpropionate were as follows. 1H-NMR (delta (ppm), CDCl3) : 0.90 (t, 3H, J=7.3Hz), 1.32 (tq, 2H, J=7.6, 7.3Hz), 1.56 (dt, 2H, J=7.6, 6.8Hz), 1.91 (s, 2H)2.64 (d, 2H, J=6.8Hz), 4.06 (t, 2H, J=6.8Hz), 4.39 (t, 1H, J=6.8Hz), 7.20-7.35 (m, 5H) 13C-NMR (delta (ppm), CDCl3) : 13.7, 19.1, 30.644.1, 52.7, 64.4, 126.2, 127.4, 128.6, 144.6, 172.0 MS (EI) m/z: 221 (M+) MS (CI, i-C4H10) m/z: 222 (MH+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a stirred suspension of (5)-3-amino-3-phenylpropionic acid (1.22 g, 7.3 mmol) and TEA (1.24 mL, 8.86 mmol) in CH2Cl2 (30 mL) at ambient temperature was added isopropyl isocyanate (0.798 mL, 8.12 mmol). The reaction mixture was stirred for 3 h, diluted with IM HCl (25 mL), and extracted with CH2Cl2 (3 * 25 mL). The combined CH2Cl2 extracts were dried over Na2SO4, filtered, and concentrated in vacuo to provide the title compound. MS: mlz =251 (M + 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium methylate; In methanol; acetone; | (1) Synthesis of (3S)-3-(2-(R,S)-hydroxydodecylamino)-3-phenylpropionic acid 27.01 g of sodium methoxide and 82.6 g of (S)-3-amino-3-phenylpropionic acid were dissolved in 800 ml of methanol. After adding 92 g of 1,2-epoxydodecane, the solution was stirred at room temperature for 20 h. Subsequently, the pH of the solution was adjusted to pH 6 with methanolic hydrochloric acid and the sodium chloride which crystallized out filtered off. After the methanol was distilled off, an oily residue remained, which crystallized in the course of stirring with 700 ml of acetone. This resulted in 153.4 g of colorless crystals. 1H NMR (DMSO) delta (ppm): 0.85 (t, 3H), 1.13-1.31 (m, 18H), 2.28/2.60/2.70/2.86 (m, 2H), 3.02 (m, 1H), 3.34 (m, 1H), 3.66-3.78 (m, 1H), 4.57 (m, 1H), 5.20/5.29 (s, br., 1H, OH), 7.42 (m, 3H), 7.60 (m, 2H), 9.40 (s, br., 2H, NH2+), 12.56 (s, 1H, CO2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.35% | With sodium tetrahydroborate; Tetrahydro-furan; compound with trifluoroborane; In tetrahydrofuran; at 30℃; for 5h;Large scale; | A solution of 1.8 kg (10.90 mol) of (s) of 3-amino-3-phenylpropionic acid was dispersed in 18 L of tetrahydrofiramide, 1.2 kg (32.68 mol) of sodium borohydride was added, and 9 kg (48-50 %, 32.68m0l) boron trifluoride-tetrahydrofuran solution, after the drop was completed, 30 C reaction 5h, stop the reaction,The reaction was quenched with 9 L of methanol, concentrated, and extracted with 4.8 L / times of ethyl acetate. The ethyl acetate layers were combined and washed twice with 4.8 L of saturated brine. Dried and concentrated to give (s) 3-amino-3-phenylpropanol. Dry weight of 1.57 kg, purity (HPLC): 99.91%, yield 95.35%. Ethyl acetate recovery cycle. |
86% | With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 0 - 66℃; for 18h;Inert atmosphere; | To a suspension of <strong>[614-19-7](S)-3-amino-3-phenylpropanoic acid</strong> (13, 16.22 g, 0.098 mol, 1.00 equiv) and NaBH4(9.46 g, 0.25 mol, 2.55 equiv) in dry THF (350 mL) at 0 C and under an argon atmosphere was added very slowly a solution of I2(30.46 g, 0.12 mol, 1.20 equiv) in dry THF (95 mL). The reaction mixture was refluxed for 18 h and then cooled to room temperature. Methanol was added drop by drop until the solution became clear. After stirring for 1 h at room temperature the solvent was removed under reduced pressure. To the residue was added 20% aqueous KOH (300 mL) and the mixture stirred for 4 h at room temperature. The aqueous phase was extracted with CH2Cl2and washed with water. The combined organic layers were dried over MgSO4and evaporated under reduced pressure to give 34 as a colorless oil (12.78 g, 0.085 mol, 86%). Rf= 0.42(MeOH/CH2Cl22:1).1H-NMR (500 MHz, CDCl3): delta = 7.32 (t, J = 7.3 Hz, 2 H), 7.27-7.21 (m, 3 H), 4.10 (dd, J = 8.5, 4.6 Hz, 1 H), 3.82-3.74 (m, 2 H), 2.67 (bs, 3 H, exchangeable with D2O), 1.92-1.81 (m, 2 H) ppm. 13C-NMR (126 MHz, CDCl3): delta = 146.1, 128.7, 127.1, 125.7, 62.3, 56.6, 39.5 ppm. MS (ESI): m/z (%) = 152.0 (110) [M + H+]. HRMS (MALDI): calcd. for C9H14NO [M + H+]: 152.10699; found 152.10678. |
With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 0℃; for 20h;Reflux; | In a 2 L three-mouth bottle by adding 500 ml tetrahydrofuran, lowering the temperature to 0 C, adding 23.0 g (0.606 muM) NaBH4, Added under mixing 50 g (S)-3 - amino -3 - phenyl propionic acid dap - 1 (303 muM). The 77 g iodine (0.303 muM) dissolved in 250 ml of tetrahydrofuran, is added to the reaction solution under stirring in the drop. Then completing, heating reflux for 20 hours, stopping the reaction, cooling, dropping 50 ml methanol quenching reaction. The organic solvent and steaming and remove, dropping 20% NaOH solution, to PH is 8 - 10, the stirring 2 h. Ethyl acetate is divided into 3 time extraction, the combined organic phase. The addition of about 10% formic acid solution stirring, liquid. In the aqueous phase by adding 70 ml 85% formic acid and 140 ml 37% formaldehyde, 90 C lower reaction 8 hours. The cooling, for 20% NaOH to adjust the PH to 8 - 10, ethyl acetate extraction three times, the combined organic phase, turns on lathe does (S)-3 - dimethyl amino -3 - phenyl propanol dap - 3 crude product. The dap - 3 crude and 37.0g1 - [...] adding 2 L three-opening in the bottle, at room temperature by adding 380 mLN, N - dimethyl formamide and 47.3 g tert-butanolate, the temperature is raised to 70 C stirring 5 h. The reaction liquid to room temperature, hexane and water added, stirring 15 minutes, standing liquid. The upper layer is cetane collected, washed with water once. Hexane phase and steaming and to remove the solvent, adding tetrahydrofuran is dissolved. Stirring next adds by drops 26.2 ml concentrated hydrochloric acid. Reaction 2 hours, steaming and remove the tetrahydrofuran and water, to the solvent-free steam, adding isopropanol, steaming and to the solvent-free steam. In the resultant product added to isopropanol, heating under stirring to make it dissolve completely. Stop heating, dropping ethyl acetate, during the dropping out of the crystal. After dropping cooling to room temperature, continuing to stir overnight, filtered, the filter cake is washed with ethyl acetate, and a ground line, N2 dry, product west reaches anchors the sandbank hydrochloride 41 g, yield 40%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With di-tert-butyl{2?-isopropoxy-[1,1?-binaphthalen]-2-yl}phosphane; potassium hydroxide; bis(dibenzylideneacetone)-palladium(0); In tert-butyl alcohol; at 90℃; for 20h;Inert atmosphere; | General procedure: An oven-dried resealable Schlenk flask was charged with Pd(dba)2 (11.4 mg, 0.02 mmol), L1 (13.6 mg, 0.03 mmol), base (3.0 mmol), and amino acid (1.20 mmol) under N2. tBuOH (2.5 mL) and aryl halides (1.00 mmol) were added in sequence via a syringe. The flask was sealed, and the mixture was allowed to heat to 90 °C for 20 h. After being cooled to room temperature, the reaction mixture was diluted with 2 mL of water and 3 mL of CHCl3, and then adjusted to pH=3 with concentrated HCl. The organic layer was separated, and the aqueous layer was extracted with CHCl3 (5 mL.x.3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated. The residual oil was purified by column chromatography on silica gel (CHCl3/CH3OH) to afford the coupling product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | General procedure: To a solution containing 100 mg (0.41 mmol) of 5 and 70.0 mg (0.82 mmol) of NaHCO3 in 4 mL of 1:1 dioxane/H2O was added 90 mg (0.45 mmol) of 4-pentenoyloxysuccinimide. The reaction mixture was stirred at room temperature for 24 h under argon. The reaction was quenched by the addition of 15 mL of 1 N aq NaHSO4 and the aqueous layer was extracted with two 25-mL portions of ethyl acetate. The combined organic extract was dried (MgSO4) and concentrated to dryness under diminished pressure. The crude product was then dissolved in 4 mL of acetonitrile. To this solution were added 300 muL (2.10 mmol) of triethylamine and 130 muL (2.10 mmol) of chloroacetonitrile. The reaction mixture was stirred at room temperature for 24 h at which time 20 mL of ethyl acetate was added. The organic layer was washed with 10 mL of 1 N aq NaHSO4 followed by 10 mL of brine, then dried (MgSO4) and concentrated to dryness under diminished pressure, affording a crude residue. The crude product was purified on a flash silica gel column (15 * 1 cm) using 1:1 ethyl acetate/hexane for elution to obtain 6 as a colorless semi-solid: yield 140 mg (38percent). |
[ 83649-48-3 ]
(R)-3-Amino-3-phenylpropanoic acid hydrochloride
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[ 83649-47-2 ]
(S)-(-)-3-Amino-3-phenylpropionic acid hydrochloride
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[ 752198-38-2 ]
(R)-3-Amino-3-(o-tolyl)propanoic acid
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[ 2061996-52-7 ]
(R)-3-Amino-3-(3,4-dimethylphenyl)propanoic acid hydrochloride
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