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CAS No. : | 3913-67-5 | MDL No. : | MFCD00037241 |
Formula : | C4H9NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GDFAOVXKHJXLEI-VKHMYHEASA-N |
M.W : | 103.12 | Pubchem ID : | 5288725 |
Synonyms : |
H-N-Me-Ala-OH
|
Num. heavy atoms : | 7 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.75 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 25.92 |
TPSA : | 49.33 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) : | -8.7 cm/s |
Log Po/w (iLOGP) : | 1.13 |
Log Po/w (XLOGP3) : | -2.49 |
Log Po/w (WLOGP) : | -0.32 |
Log Po/w (MLOGP) : | -2.61 |
Log Po/w (SILICOS-IT) : | -0.67 |
Consensus Log Po/w : | -0.99 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 3.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 1.22 |
Solubility : | 1720.0 mg/ml ; 16.6 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 2.0 |
Solubility : | 10200.0 mg/ml ; 99.3 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -0.06 |
Solubility : | 90.9 mg/ml ; 0.881 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.19 |
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 |
---|---|---|
45% | With N-ethyl-N,N-diisopropylamine In dichloromethane | To 50.2 mg of N-methyl-L-alanine suspended in 60 ml of CH2Cl2 was added 0.186 ml of DIPEA. After the solid mass had been broken up into a fine suspension by sonication, 82.6 mg of 1,1'-carbonyldiimidazole was added in 5 portions over 4 hours. The reaction was stirred over night, then filtered through a short silica column with dichloromethane. The filtrate was evaporated and crystallized with ether/hexane to afford 28 mg (45percent Yield) of product. 1H NMR (DMSO) 4.40 (1H, dd, J=7.0, 14.1 Hz, CH), 2.84 (3H, s, N-CH3), 1.38 (3H, d, J=7.1 Hz); 13C NMR 194.83, 184.18, 56.70, 27.97, 14.09; MS M-168.8 (M+K-1), 153.8 (M+Na-1). Compound Id can be prepared in a similar manor from N-methyl-D-alanine. Compound Ic can also be prepared by the reaction of phosgene on N-methyl-L-alanine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In 1,4-dioxane; for 18h; | To a solution of 8-((R)-1-phenyl-propylcarbamoyl)-3,4-dihydro-1 H-pyrrolo[2,1-c][1,4]oxazine-6-carboxylic acid (comp. no. 11a) (100 mg, 0.335 mmol) in dimethylformamide (2.2 ml) was added 1-hydroxybenzotriazole (45 mg, 0.335 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (64 mg, 0.335 mmol). The mixture was stirred for 1 h at 25C, then (S)-2-methylamino-propionic acid ethyl ester hydrochloride (56 mg, 0.335 mmol) (prepared from (S)-2-methylamino-propionic acid by heating in ethanol and 4 M hydrogen chloride in dioxane for 18 h and evaporation of the solvents) and triethylamine (62 mg, 0.61 mmol) were added and the mixture was stirred at 25C overnight. Another portion of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (13 mg, 0.067 mmol) and (S)-2-methylamino-propionic acid ethyl ester hydrochloride (12 mg, 0.067 mmol) were added and the mixture was stirred for 1 h. After filtration of the mixture through a short filter cartridge the solution was purified by reverse phase HPLC (acetonitrile/water gradient with 0.1 % trifluoroacetic acid) to give 68 mg (51 %) (S)-2-{Methyl-[8-((R)-1-phenyl-propylcarbamoyl)-3,4-dihydro-1 H-pyrrolo[2,1-c][1,4]oxazine-6-carbonyl]-amino}-propionic acid ethyl ester. LC/MS (method 2): Rt = 1 .1 1 min; m/z = 442.3 (M+H+). 1H-NMR: delta (ppm) = 8.46 (1 H, t), 8.21 (1 H, d), 7.35-7.36 (3H, m), 7.30 (2H, t), 7.21 (1 H, t), 4.91 (2H, dd), 4.82 (1 H, q), 4.19 (2H, t), 4.1 1 (2H, q), 3.90- 3.92 (4H, m), 1 .71 -1 .83 (2H, m), 1 .21 (3H, t), 0.88 (3H, t). | |
With thionyl chloride; In neat (no solvent); at 0 - 25℃; for 16h; | To a solution of (2S)-2-(methylamino)propanoic acid (1 g, 9.70 mmol) in EtOH (10 mL) was added SOCl2 (1.50 g, 12.61 mmol) dropwise at 0 C in 0.5 hr. The reaction mixture was stirred at 25 C for 15.5 hrs, then diluted with EA (20 mL), washed with H20 (5 mL) and brine (5 mL). The organic layer was dried over Na2S04 and concentrated in vacuo. Ethyl (2S)-2- (methylamino)propanoate hydrochloride (1.8 g, Compound AS-1) was obtained as a yellow oil and used for next step without further purification. | |
1.8 g | With thionyl chloride; at 0 - 25℃; for 16h; | To a solution of (2S)-2-(methylamino)propanoic acid (1 g, 9.70 mmol) in EtOH (10mL) was added SOd2 (1.50 g, 12.61 mmol) dropwise at 0 C in 0.5 hr. The reactionmixture was stirred at 25 C for 15.5 hrs, then diluted with EA (20 mL), washed with H20(5 mL) and brine (5 mL). The organic layer was dried over Na2SO4 and concentrated invacuo. Ethyl (2S)-2-(methylamino)propanoate hydrochloride (1.8 g, Compound AS-1) was obtained as a yellow oil and used for next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tetrahydroborate; iodine; In tetrahydrofuran; for 18h;Cooling with ice; Reflux; | A solution of iodine (4.92 g, 19.39 mmol) in tetrahydrofuran (10 mL) was slowly added dropwise to a suspension of N-methyl-L-alanine (2.00 g, 10.39 mmol) and sodium borohydride (1.83 g, 48.49 mmol) in tetrahydrofuran (50 mL), pre-cooled in an ice-bath. Once the addition was complete the reaction mixture was heated to reflux. After 18 h the reaction was allowed to cool to ambient temperature and then methanol (5 mL) was slowly added. The mixture was stirred at ambient temperature for 30 minutes and then concentrated under reduced pressure. The residue was dissolved in 20% KOH (w/w) (30 mL) and then stirred at ambient temperature for 4 hours. The aqueous reaction mixture was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to provide a clear oil (2.07 g, 100% yield). | |
With sodium tetrahydroborate; iodine; In tetrahydrofuran; for 18h;Cooling with ice; Reflux; | 0264] A solution of iodine (4.92 g, 19.39 mmol) in tetrahydrofuran (10 mL) was slowly added dropwise to a suspension of /V-methyl-L-alanine (2.00 g, 10.39 mmol) and sodium borohydride (1.83 g, 48.49 mmol) in tetrahydrofuran (50 mL), pre-cooled in an ice-bath. Once the addition was complete the reaction mixture was heated to reflux. After 18 h the reaction was allowed to cool to ambient temperature and then methanol (5 mL) was slowly added. The mixture was stirred at ambient temperature for 30 min and then concentrated under reduced pressure. The residue was dissolved in 20% potassium hydroxide (w/w) (30 mL) and then stirred at ambient temperature for 4 h. The aqueous reaction mixture was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to provide a clear oil (2.07 g, 100% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.12 g | 200 mL of ethylene glycol dimethyl ether aqueous solution (ethylene glycol dimethyl ether: water = 1: 1) was prepared and N-methyl-L-alanine (3.85 g, 37.4 mmol) was dissolved in 100 mL of ethylene glycol dimethyl Ether solution. To the reaction system, 14.5 g of triethylamine was added and stirred vigorously for 5 min. 9b (9.33g, 37.4mmol) was dissolved in 80mL of ethylene glycol dimethyl ether aqueous solution, as constant pressure dropping funnelIn the reaction system was slowly added dropwise within 10min drops, the dropping process, the reaction system gradually turn yellow, stirring was completed overnight. After the reaction was completed, the reaction system was concentrated to about 100 mL, 25 mL of deionized water was added, and the pH was adjusted to 2.0 with 6 mol / LHCl. The system turned cloudy. The mixture was extracted with ethyl acetate (80 mL × 3). The organic phases were combined and the organic phase was washed with 25 mL of saturated aqueous sodium chloride. The organic phase was collected and dried over anhydrous sodium sulfate. The filtrate was concentrated to give 5.32 g of a yellow oil, which was subjected to column chromatography after concentration of the organic phase. The mobile phase was PE: EA = 1: 1. The desired fractions were collected and concentrated to give 1.12 g of a white solid.3) Synthesis of 5b |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Intermediate 4: lambda/-{r3-(4-{r4-r5-Fluoro-2-(methyloxy)phenyl1-2-hvdroxy-4-methyl-2- (trifluoromethyl)pentyl1amino>-6-methyl-1 /-/-indazol-1-yl)phenyl1carbonyl>-lambda/-methyl-L- alanine; lambda/,lambda/-Diisopropylethylamine (0.149ml_, 0.855mmol) and HATU (68.3mg, 0.18mmol) were added to a solution of 3-(4-[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2- (trifluoromethyl)pentyl]amino}-6-methyl-1 /-/-indazol-1-yl)benzoic acid (96mg, 0.171 mmol) in DMF (1 mL) and the solution stirred at room temperature under nitrogen for 10 min. N- methyl-L-alanine (44.1 mg, 0.43mmol) was added and the mixture stirred at room temperature for 5 days. The resulting suspension was diluted with methanol and DMSO to give a solution which was filtered and purified by mass directed autopreparation (System B) to give the title compound (40.9mg). LCMS: tRET = 3.79 min; MH+ = 645 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With triethylamine; In 1,2-dimethoxyethane; water; for 2.08333h; | N-methyl-N-(4-methyl-4-methyldithio-1-oxopentyl)-L-alanine (10): <strong>[3913-67-5]N-Methyl-L-alanine</strong> (2.85 g, 18.0 mmol) was dissolved in 50 mL of a 1:1 solution of dimethoxyethane and deionized water in a 125 mL flask equipped with a magnetic stir bar. Triethylamine (6.9 g, 36 mmol) was added and the solution was vigorously stirred as 9 (5.44 g, 18 mmol) dissolved in 40 mL of the same solvent mixture was added drop-wise over approximately 5 min. After 2 hours the reaction mixture was concentrated to approximately 40 mL by rotary evaporation under vacuum, then 10 mL of deionized water and 1 M HCl were added to give a pH of approximately 2. The mixture was poured into a separatory funnel and extracted twice with 50 mL portions of ethyl acetate. The organic layers were combined and then washed with 7 mL of saturated sodium chloride solution. The organic layer was dried over 8.0 g of anhydrous Na2SO4 and the solvent was removed by rotary evaporation under vacuum. The residue was taken up in a minimum volume of ethyl acetate and purified by chromatography on silica (silica: 40 micron flash grade, silica bed: 24*3.0 cm, mobile phase: hexanes:ethyl acetate:acetic acid 50:48:2). Fractions containing desired product were combined and solvent was removed under vacuum. Residual acetic acid was removed by dissolving the residue in a minimum volume of ethyl acetate and precipitating product by the rapid but drop-wise addition of hexane with stirring. Hexane was added until product was no longer detected in the supernatant by TLC analysis. The precipitate was vacuum dried for 4 hours to give 2.2 g of product 10 (51% yield). 1H NMR (CDCl3): delta1.32 (6H, s), 1.42 (3H, d, J=7 Hz), 1.90-97 (2H, m), 2.40 (3H, s), 2.42-2.49 (2H, m), 2.9 (3H, s), 5.15 (1H, q, J=7 Hz). MS (M+Na+) calc.: 302.1, found: 302.0._ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With N-ethyl-N,N-diisopropylamine; In dichloromethane;Product distribution / selectivity; | To 50.2 mg of N-methyl-L-alanine suspended in 60 ml of CH2Cl2 was added 0.186 ml of DIPEA. After the solid mass had been broken up into a fine suspension by sonication, 82.6 mg of 1,1'-carbonyldiimidazole was added in 5 portions over 4 hours. The reaction was stirred over night, then filtered through a short silica column with dichloromethane. The filtrate was evaporated and crystallized with ether/hexane to afford 28 mg (45% Yield) of product. 1H NMR (DMSO) 4.40 (1H, dd, J=7.0, 14.1 Hz, CH), 2.84 (3H, s, N-CH3), 1.38 (3H, d, J=7.1 Hz); 13C NMR 194.83, 184.18, 56.70, 27.97, 14.09; MS M-168.8 (M+K-1), 153.8 (M+Na-1). Compound Id can be prepared in a similar manor from N-methyl-D-alanine. Compound Ic can also be prepared by the reaction of phosgene on N-methyl-L-alanine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Product distribution / selectivity; | To 50.2 mg of N-methyl-L-alanine suspended in 60 ml of CH2Cl2 was added 0.186 ml of DIPEA. After the solid mass had been broken up into a fine suspension by sonication, 82.6 mg of 1,1'-carbonyldiimidazole was added in 5 portions over 4 hours. The reaction was stirred over night, then filtered through a short silica column with dichloromethane. The filtrate was evaporated and crystallized with ether/hexane to afford 28 mg (45% Yield) of product. 1H NMR (DMSO) 4.40 (1H, dd, J=7.0, 14.1 Hz, CH), 2.84 (3H, s, N-CH3), 1.38 (3H, d, J=7.1 Hz); 13C NMR 194.83, 184.18, 56.70, 27.97, 14.09; MS M-168.8 (M+K-1), 153.8 (M+Na-1). Compound Id can be prepared in a similar manor from N-methyl-D-alanine. Compound Ic can also be prepared by the reaction of phosgene on N-methyl-L-alanine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In methanol; | a) <strong>[3913-67-5]N-Methyl-L-alanine</strong>-methyl ester hydrochloride. To a solution of <strong>[3913-67-5]N-Methyl-L-alanine</strong> (0.2g, 2 mmol) in MeOH (5 mL) was bubbled HCI (gas) for 2 min. The resulting mixture was stirred at room temperature for 24h. The solvent was removed in vacuum to give a title compound as a solid (0.38 mg. 100%). MS (ES+) m/e 118[M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With triethylamine; In tetrahydrofuran; water; | N-methyl-N-(4-methyldithio-butanoyl)-L-alanine (5c). To a stirred solution of 4-methyldithiobutanoic acid (3c) (0.200 g, 1.20 mmol) in dry THF (10 ml) at -20 C. under Argon was added isobutyl chloroformate (0.164 g, 1.20 mmol) and triethylamine (0.121 g, 1.20 mmol) and the mixture was stirred for twenty minutes. A mixture of N-methyl-L-alanine (0.124 g, 1.20 mmol) and triethylamine (0.243 g, 2.40 mmol) in water (5 ml) was then added and the reaction mixture was stirred at room temperature for five hours. The reaction mixture was then treated as described above for 5b giving the title compound as white crystals (0.135 g, 44%): mp 92-93 C. 1 H NMR (CDCl3) delta1.4 (3H, d), 2.0 (2H, m), 2.3 (3H, s), 2.7 (4H, m), 2.9 (3H, s), 5.1 (1H, q), 10.5 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With triethylamine; In tetrahydrofuran; water; | N-methyl-N-(5-methyldithio-pentanoyl)-L-alanine (5d). To a stirred solution of 5-methyldithio-pentanoic acid (3d) (0.202 g, 1.12 mmol) in dry THF (15 ml) at -40 C. under Argon was added isobutyl chloroformate (0.153 g, 1.12 mmol) and triethylamine (0.113 g, 1.12 mmol) and the reaction mixture was stirred for 20 minutes at -10 C. A solution of N-methyl-L-alanine (0.116 g, 1.12 mmol) and triethylamine (0.227 g, 2.24 mmol) in water (5 ml) was then added and the mixture was stirred at 0 C. for five hours. The reaction mixture was treated as described above for 5b affording the title compound as white crystals (0.196 g, 66%): mp 84 C. 1 H NMR (CDCl3) delta1.4 (3H, d), 1.8 (4H, m), 2.4 (3H, s), 2.7 (4H, m), 3.0 (3H, s), 5.2 (1H q), 10.7 (1H, s). |
66% | With triethylamine; In tetrahydrofuran; water; | N-methyl-N-(5-methyldithio-pentanoyl)-L-alanine (6d). To a stirred solution of 5-methyldithio-pentanoic acid (4d) (0.202 g, 1.12 mmol) in dry THF (15 mL) at -40 C. under argon was added isobutyl chloroformate (0.153 g, 1.12 mmol) and triethylamine (0.113 g, 1.12 mmol) and the reaction mixture was stirred for 20 minutes at -10 C. A solution of N-methyl-L-alanine (0.116 g, 1.12 mmol) and triethylamine (0.227 g, 2.24 mmol) in water (5 mL) was then added and the mixture was stirred at 0 C. for five hours. The reaction mixture was treated as described above for 6b affording the title compound as white crystals (0.196 g, 66%): mp 84 C. 1H NMR (CDCl3) delta1.4 (3H, d), 1.8 (4H, m), 2.4 (3H, s), 2.7 (4H, m), 3.0 (3H, s), 5.2 (1H, q), 10.7 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With hydrogenchloride; triethylamine; In tetrahydrofuran; water; | N-Methyl-N-(3-phenyldithio-propanoyl)-L-alanine (5e). A solution of 3-phenyldithio-propanoic acid (4a) (1.8 g, 8.4 mmol) in dry THF was stirred vigorously under a nitrogen atmosphere and cooled to -15 C. Isobutyl chloroformate (1.2 ml, 9.25 mmol) and triethylamine (1.29 ml, 9.25 mmol) were added and the reaction mixture was stirred at this temperature for ten minutes. A solution of N-methyl-L-alanine (0.87 g, 8.4 mmol) and triethylamine (1.29 ml, 9.25 mmol) in water (10 ml) was then added and the reaction mixture was stirred for fifteen minutes at -15 C. and then warmed to room temperature and stirred for an additional period of 2.5 hours. 1M HCl (10 ml) was added and the reaction mixture was extracted with ethyl acetate (4*50 ml). The combined organic layers were dried with Na2 SO4, filtered and evaporated under reduced pressure. The crude mixture was purified by column chromatography on silica gel eluding with ethyl acetate/hexane-containing 2% acetic acid to give a white solid (1.5 g, 60%): mp 96-97 C. NMR (CDCl3 /TMS) delta1.4 (2H, d), 2.7-3.0 (7H, m), 5.2 (1H, q), 7.2-7.6 (5H, m). |
60% | With hydrogenchloride; triethylamine; In tetrahydrofuran; water; | N-Methyl-N-(3-phenyldithio-propanoyl)-L-alanine (6e). A solution of 3-phenyldithio-propanoic acid (5a) (1.8 g, 8.4 mmol) in dry THF was stirred vigorously under a nitrogen atmosphere and cooled to -15 C. Isobutyl chloroformate (1.2 mL, 9.25 mmol) and triethylamine (1.29 mL, 9.25 mmol) were added and the reaction mixture was stirred at this temperature for ten minutes. A solution of N-methyl-L-alanine (0.87 g, 8.4 mmol) and triethylamine (1.29 mL, 9.25 mmol) in water (10 mL) was then added and the reaction mixture was stirred for fifteen minutes at -15 C. and then warmed to room temperature and stirred for an additional period of 2.5 hours. 1 M HCl (10 mL) was added and the reaction mixture was extracted with ethyl acetate (4*50 mL). The combined organic layers were dried with Na2SO4, filtered, and evaporated under reduced pressure. The crude mixture was purified by column chromatography on silica gel eluding with ethyl acetate/hexane-containing 2% acetic acid to give 6e a white solid (1.5 g, 60%): mp 96-97 C. 1H NMR (CDCl3/TMS) delta1.4 (2H, d), 2.7-3.0 (7H, m), 5.2 (1H, q), 7.2-7.6 (5H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.556 g (34%) | With triethylamine; In tetrahydrofuran; water; | N-methyl-N-(3-methyldithio-propanoyl)-L-alanine (5b). To a stirred solution of 3-methyldithiopropanoic acid (3b) (1.00 g, 6.57 mmol) in dry THF (20 ml) at -10 C. under argon was added isobutylchloroformate (0.897 g, 6.57 mmol) and triethylamine (0.665 g, 6.57 mmol) and the reaction mixture was stirred for 15 minutes. A mixture of N-methyl-L-alanine (0.677 g, 6.57 mmol) and triethylamine (1.33 g, 13.14 mmol) in water (10 ml) was added and the reaction mixture was stirred at room temperature overnight. The mixture was then diluted with water (50 ml), acidified (aqueous HCl), and extracted with ethyl acetate (4*50 ml). The combined organic layers were dried over sodium sulfate, the solvent evaporated under reduced pressure and the residue chromatographed over silica gel eluding with methylene chloride/ethyl acetate to yield 0.556 g (34%) white crystals: mp 98-100 C. 1 H NMR (CDCl3) delta1.3 (3H, d), 2.2 (3H, s), 2.7 (4H, m), 4.5 (1H, q), 10.7 (1H, s). Anal. Calculated for C8 H15 NO3 S2: C, 40.49; H, 6.37; N, 5.90; mol wt. 237.33. Found: C, 40.42; H, 6.41; N, 5.93. |
0.556 g (34%) | With triethylamine; In tetrahydrofuran; water; | N-methyl-N-(3-methyldithio-propanoyl)-L-alanine (6b). To a stirred solution of 3-methyldithio-propanoic acid (4b) (1.00 g, 6.57 mmol) in dry THF (20 mL) at -10 C. under argon was added isobutylchloroformate (0.897 g, 6.57 mmol) and triethylamine (0.665 g, 6.57 mmol) and the reaction mixture was stirred for 15 minutes. A mixture of N-methyl-L-alanine (0.677 g, 6.57 mmol) and triethylamine (1.33 g, 13.14 mmol) in water (10 mL) was added and the reaction mixture was stirred at room temperature overnight. The mixture was then diluted with water (50 mL), acidified (aqueous HCl), and extracted with ethyl acetate (4*50 mL). The combined organic layers were dried over sodium sulfate, the solvent evaporated under reduced pressure and the residue chromatographed over silica gel eluding with methylene chloride/ethyl acetate to yield 0.556 g (34%) white crystals: mp 98-100 C. 1H NMR (CDCl3) delta1.3 (3H, d), 2.2 (3H, s), 2.7 (4H, m), 4.5 (1H, q), 10.7 (1H, s). Anal. calculated for C8H15NO3S2:C, 40.49; H, 6.37; N, 5.90; mol wt. 237.33. Found: C, 40.42; H, 6.41; N, 5.93. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.048 g (36%) | With triethylamine; In tetrahydrofuran; | N-Methyl-N-[3-(4-Nitrophenyldithio)-propanoyl]L-alanine (5f). To a stirred solution of 3-(4-nitrophenyldithio)-propanoic acid (4b) (0.100 g, 0.386 mmol) in dry THF (10 ml) at -40 C. under argon was added isobutyl chloroformate (0.053 g, 0.386 mmol) and triethylamine (0.039 g, 0.38 mmol) and the reaction stirred at 0 C. for sixty minutes. An aqueous solution (5 ml) of N-methyl-L-alanine (0.040 g, 0.386 mmol) and triethylamine (0.039 g, 0.386 mmol) was then added and the mixture stirred at 0 C. for five hours. The mixture was diluted with water (50 ml), acidified (aqueous HCl), and extracted with ethyl ether (3*25 ml). The combined organic layers were dried (Na2 SO4), and the solvent evaporated under reduced pressure. The residue was chromatographed over silica gel eluding with methylene chloride/ethyl acetate to yield 0.048 g (36%) yellow crystals: mp 74-77 C. NMR (CDCl3) delta1.4 (3H, d), 2.6-3.4 (4H, m), 2.9 (3H, s), 5.1 (1H, q), 7.6-8.3 (4H, 2d). |
0.048 g (36%) | With triethylamine; In tetrahydrofuran; | N-Methyl-N-[3-(4-nitrophenyldithio)-propanoyl]-L-alanine (6f). To a stirred solution of 3-(4-nitrophenyldithio)-propanoic acid (5b) (0.100 g, 0.386 mmol) in dry THF (10 mL) at -40 C. under argon was added isobutyl chloroformate (0.053 g, 0.386 mmol) and triethylamine (0.039 g, 0.38 mmol) and the reaction stirred at 0 C. for one hour. An aqueous solution (5 mL) of N-methyl-L-alanine (0.040 g, 0.386 mmol) and triethylamine (0.039 g, 0.386 mmol) was then added and the mixture stirred at 0 C. for five hours. The mixture was diluted with water (50 mL), acidified (aqueous HCl), and extracted with ethyl ether (3*25 mL). The combined organic layers were dried (Na2SO4), and the solvent evaporated under reduced pressure. The residue was chromatographed over silica gel eluding with methylene chloride/ethyl acetate to yield 0.048 g (36%) yellow crystals: mp 74-77 C. 1H NMR (CDCl3) delta1.4 (3H, d), 2.6-3.4 (4H, m), 2.9 (3H, s), 5.1 (1H, q), 7.6-8.3 (4H, 2d). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2-(Dimethylamino)pyridine; triethylamine; In dichloromethane; toluene; | (C) (S)-N-[[3-[[(Phenylmethoxy)carbonyl]amino]-2-oxo-1-azetidinyl]carbonyl]N-methyl-DL-alanine, phenylmethyl ester A solution of phosgene in toluene (4.7 ml of a 20% solution, 9.36 mmol) was cooled to -25 C. under argon. While stirring, a solution (pre-cooled to 0 C.) of N-methyl-DL-alanine, benzyl ester (1.0 g, 5.2 mmol) and triethylamine (870 mul, 6.25 mmol) in dichloromethane (5 ml) was added over 5 minutes maintaining the temperature at -20 to -25 C. After stirring at -25 C. for 1 hour, solvent and excess phosgene were removed in vacuo. The residue was dissolved in dichloromethane (12 ml), cooled to 0 C. and then (S)-3-[[(phenylmethoxy)carbonyl]amino]-2-azetidinone (1.15 g, 5.2 mmol), dimethylaminopyridine (63 mg, 0.52 mmol), and triethylamine (870 mul, 6.2 mmol) were added sequentially. Stirring was continued for 10 minutes at 0 C. and then overnight at room temperature. After refluxing for an additional 7 hours, the mixture was again stirred overnight at room temperature. The mixture was washed with water, dried (Na2 SO4) and solvent was removed in vacuo. The resulting oil was chromatographed on silica gel eluding with a 4:6 ethyl acetate:hexane mixture. The desired product was obtained as an oil (580 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In methanol; | (i) In 600 ml of methanol is suspended 53.5 g (0.52 mole) of N-methyl-L-alanine, and under ice-cooling and stirring, 76 g of dry hydrogen chloride gas is dissoled. The suspension of the starting material is liquidated with the progress of the reaction, and after stirring at the room temperature overnight, a homogeneous solution is obtained. After 85 g (0.8 mole) of methyl orthoformate is added, the reaction mixture is further allowed to stand at a room temperature for 24 hours. A small amount of insolubles is filtered off and the filtrate is concentrated under reduced pressure. By the above procedure there is obtained the hydrochloride of N-methyl-L-alanine methyl ester as a solid product. NMR spectrum (in DMSO-d6) delta: 1.50(3H, d, J=7 Hz), 2.60(3H, m; after addition of D2 O, s), 3.75(3H, s), 4.12(1H, m; after addition of D2 O, q, J=7 Hz), 9.83(2H, br.). | |
With hydrogenchloride; In methanol; | (i) In 600 ml of methanol was suspended 53.5 g (0.52 mole) of N-methyl-L-alanine, and under ice-cooling and stirring, 76 g of dry hydrogen chloride gas was dissolved. The suspension of the starting material was liquidated with the progress of the reaction, and after stirring at room temperature overnight, a homogeneous solution was obtained. After 85 g (0.8 mole) of methyl orthoformate was added, the reaction mixture was further allowed to stand at room temperature for 24 hours. The minor amounts of insolubles were filtered off and the filtrate was concentrated under reduced pressure. By the above procedure there was obtained the hydrochloride of N-methyl-L-alanine methyl ester as a solid product. NMR spectrum (in DMSO-d6) delta: 1.50(3H, d, J=7 Hz), 2.60(3H, m; after addition of D2 O, s), 3.75(3H, s), 4.12(1H, m; after addition of D2 O, q, J=7 Hz), 9.83(2H, br.) | |
With hydrogenchloride; In methanol; | EXAMPLE 22 In 600 ml of methanol was suspended 53.5 g (0.52 mol) of N-methyl-L-alanine and under ice-cooling and stirring, 75 g of dry hydrogen chloride gas was dissolved. The suspension of the starting material cleared gradually with reaction time and, on stirring overnight, yielded a homogeneous solution. To the reaction mixture was added 85 g (0.8 mol) of methyl orthoformate and the mixture was allowed to stand at room temperature for 24 hours. The small quantities of insolubles were filtered off and the filtrate was concentrated under reduced pressure. By the above procedure was obtained a solid product of N-methyl-L-alanine methyl ester hydrochloride. NMR spectrum(DMSO-d6) delta: 1.50(3H,d,J=7Hz), 2.60(3H,m; after addition of deuterium oxide, s), 3.75(3H,s), 4.12 (1H,m; after addition of deuterium oxide, q,J=7HZ), 9.83(2H,br.) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With triethylamine; In tetrahydrofuran; water; | N-methyl-N-(4-methyldithio-butanoyl)-L-alanine (6c). To a stirred solution of 4-methyldithio-butanoic acid (4c) (0.200 g, 1.20 mmol) in dry THF (10 mL) at -20 C. under argon was added isobutyl chloroformeta (0.164 g, 1.20 mmol) and triethylamine (0.121 g, 1.20 mmol) and the mixture was stirred for twenty minutes. A mixture of N-methyl-L-alanine (0.124 g, 1.20 mmol) and triethylamine (0.243 g, 2.40 mmol) in water (5 mL) was then added and the reaction mixture was stirred at room temperature for five hours. The reaction mixture was then treated as described above for 6b giving the title compound as white crystals (0.135 g, 44%): mp 92-93 C. 1H NMR (CDCl3) delta1.4 (3H, d), 2.0 (2H, m), 2.3 (3H, s), 2.7 (4H, m), 2.9 (3H, s), 5.1 (1H, q), 10.5 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | A 250 ml two-necked flask, under a nitrogen atmosphere, was successively charged with: 10 g (97 mmol) of (L)-<strong>[3913-67-5]N-methylalanine</strong>, then 200 ml of a 1 M aqueous solution of NaOH (200 mmol, 2.06 eq.). The white suspension thus obtained was stirred until it had completely dissolved (around 30 minutes). This solution was cooled to around 3 C. using a water/ice bath and, with vigorous stirring (around 750 rpm), 15 ml of methyl chloroformate (192 mmol, 1.98 eq.) were added over around 30 minutes using a 50 ml dropping funnel. The two-phase medium thus obtained was stirred at 3 C.After 6 hours, the temperature of the reaction medium was raised to around 20 C. by removing the ice/water bath, and the pH of the reaction medium was brought to around 1 (measured with pH paper) using 37% aqueous HCl. This aqueous phase was then extracted with 3 times 50 ml of AcOEt. The organic phases were combined, washed with 50 ml of demineralized water, then dried over around 10 g of anhydrous MgSO4. The medium was filtered through sintered glass, then the filtrate was concentrated to dryness under vacuum (temperature of the bath at around 35 C., vacuum of around 40 mbar). Thus, 13.4 g (86%) of product were obtained in the form of a colourless viscous oil.Structural analyses: LC-MS-DAD-ELSD: 160(-)=(M-H)(-), 162(+)=(M+H)(+); 1H NMR (DMSO-d6 at 400 MHz): for this batch, a 60-40% mixture of conformational isomers was observed, with: 1.31 (d, J=7.5 Hz, 3H); 2.78 (s, 3H); 3.58 (s, 1.2H); 3.60 (s, 1.8H); 4.50 (q, J=7.5 Hz, 0.4H); 4.58 (q, J=7.5 Hz, 0.6H); 10.7 (broad m, 1H).Analysis by gas chromatography on a chiral column made it possible to show that the enantiomeric excess of the <strong>[3913-67-5]N-methylalanine</strong> methyl carbamate was >99%. The conditions for the chromatographic analysis are given below: RT-Gammadex column (30 m/0.25 mm/0.25 mum); isotherm at 120 C. (3 min), then 5 C./min to 180 C., isotherm at 180 C. (3 min); injection split 1:25; helium carrier gas at 1.8 ml/min; FID detection; solution at a concentration of 2 mg/ml in CH2Cl2, esterification with 0.2 M TMSH. Under these conditions, the (L)-<strong>[3913-67-5]N-methylalanine</strong> methyl carbamate had a retention time rt=8.8 min. The other enantiomer, (D)-<strong>[3913-67-5]N-methylalanine</strong> methyl carbamate, had a retention time rt=8.5 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; In acetone; at 40℃; for 90h; | General procedure: Each amino acid was added with 0.1% solution of Nalpha-(5-fluoro-2,4-dinitrophenyl)-l-alaninamide (l-FDAA, Marfey's reagent, 200 muL) in acetone and 0.5M NaHCO3 (100 muL) followed by heating at 40 C for 90 min. After cooling to room temperature, the reaction mixture was neutralized with 2N HCl (25 muL) and diluted with MeOH (300 muL). The solution was subjected to reversed-phase HPLC [Cosmosil 5C18-AR-II (4.6×250 mm), MeOH/20 mM AcONa=55:45 (solvent A) or 45:55 (solvent B) at 1.0 mL/min, UV detection at 340 nm]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With hydrogen;palladium 10% on activated carbon; In methanol; under 775.743 Torr; for 18h; | N-Me-Ala-OH (2.0g, 15.5mmol) was dissolved in methanol (200mls), acetone (1.3g, 23.2mmol) was added followed by 10% Pd/C (1.5g). The reaction mixture was shaken at 15 psi for 18 hours. After this time the catalyst was filtered off through Celite and the residue washed with MeOH (lOOmls). The combined filtrates were evaporated in vacuo to give a white solid which was recrystallised from MeOH/diethyl ether to give a white crystalline solid identified as the title compoundYield = 2.48g, 17.1mmol, 88% [M+H]+ = 146.36 |
88% | With hydrogen;palladium 10% on activated carbon; In methanol; under 775.743 Torr; for 18h; | N-Me-Ala-OH (2.0g, 15.5mmol) was dissolved in methanol (200mls), acetone (1.3g, 23.2mmol) was added followed by 10% Pd/C (1.5g). The reaction mixture was shaken at 15 psi for 18 hours. After this time the catalyst was filtered off through Celite and the residue washed with MeOH (lOOmls). The combined filtrates were evaporated in vacuo to give a white solid which was recrystallised from MeOH/diethyl ether to give a white crystalline solid identified as the title compoundYield = 2.48g, 17.1mmol, 88%[M+H]+ = 146.36 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; In water; acetone; at 80℃; for 0.05h; | General procedure: To the solution of each fraction in H2O (50 L) was added 0.1 % L-FDLA acetone sol. (100 L) and 1 M NaHCO3 (25 L). The mixture was heated at 80 C for 3 minutes, cooled to the room temperature and neutralized with 1 M HCl. The each product was analyzed by HPLC and the retention times were compared to those of L-FDLA derivatized authentic standards. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; water; at 110℃; for 18h; | General procedure: A sample of compound 1 (1.0 mg) was treated with 6 N HCl (1 mL) at 110 C for 18 h. The resulting hydrolysate was concentrated to dryness, re-dissolved in H2O (0.6 mL) and divided into two equal portions. Each portion was combined with either a 1% solution of 1-fluoro-2,4-dinitrophenyl-5-L-alaninamide (L-FDAA, Marfey's reagent, 50 muL) in acetone or a racemic mixture of a 1% solution of 1-fluoro-2,4-dinitrophenyl-5-LD-alaninamide (LD-FDAA, 50 muL) in acetone and 1 M NaHCO3 (25 muL), and the two mixtures were heated at 40 C for 45 min. Both reaction mixtures were cooled to r.t. and quenched by the addition of 2 N HCl (25 muL), dried, and redissolved in MeCN (500 lL). The aliquots were subjected to reversed-phase LC-MS (Agilent 1100 series) according to the advanced Marfey's method (Phenomenex, Luna, 150 x 2.0 mm, 5 mum, 100 A; MeCN in 0.1% (v/v) aqueous HCOOH; at 0.20 mL/ min) using a linear gradient (10-50% MeCN over 60 min) (Marfey, 1984; Fuji et al., 1997a,b). An Agilent 1100 series MSD spectrometer was used for detection in ESI (negative mode). The retention times and ESIMS product ions (tR in min, m/z[M-H]-) of the L-FDAA-derivatized amino acids in the hydrolysate of the first portion were observed to be Ile (45.1, 382.0), N-Me-Phe (48.6, 430.1), Ala(28.3.0, 340.0), and N-Me-Ala (35.2, 354.0). The reaction with racemic LD-FDAA in the second portion gave rise to two peaks for each corresponding amino acid moiety and the retention times and ESIMS product ions (tR1/tR2, min, m/z [M-H]-) were observed to be Ile (45.1/52.4, 382.0), N-Me-Phe (47.9/48.6, 430.1), Ala (28.3/ 49.5, 340.0), and N-Me-Ala (35.2/36.1, 354.0). Consequently, the absolute configurations of the moieties in the hydrolysate of 1 were confirmed as D-N-Me-Phe, L-Ala, and L-N-Me-Ala. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Another exemplary embodiment is bra-hex-ala-May 8 of and Example 2 where E is 2-bromoacetamide, and n is 5. Acylation of 2,5-dioxopyrrolidin-1-yl 6-(2-bromoacetamido)hexanoate 6 with (S)-2-(methylamino)propanoic acid (N-methyl S-alanine) 2 gave (S)-2-(6-(2-bromoacetamido)-N-methylhexanamido)propanoic acid 7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Amidation of 12 with (S)-2-(methylamino)propanoic acid (N-methyl S-alanine) 2 gave (S)-1-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-19,20-dimethyl-13,18-dioxo-3,6,9-trioxa-12,19-diazahenicosan-21-oic acid 13. | ||
Amidation of 12 with (S)-2-(methylamino)propanoic acid (N-methyl S-alanine) 2 gave (S)-1-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-19,20-dimethyl-13,18-dioxo-3,6,9-trioxa-12,19-diazahenicosan-21-oic acid 13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; phosphorus pentachloride; In dichloromethane; at 0 - 20℃; for 15h; | Synthesis of N-methyl-L-alanine Allyl Ester Hydrochloride (257.HCl)4M HCl-dioxane (3.0 mL) was added to a suspension of N-methyl L-alanine (256, 1.05 g, 10.1 mmol) in CH2Cl2 (16 mL). PCl5 (2.54 g, 12.2 mmol) was added portionwise at 0 C. The mixture was allowed to warm to rt over 15 h. The volatiles were evaporated. The residue was dissolved in CH2Cl2 (10 mL) and allyl alcohol (0.83 mL, 12.2 mmol) was added dropwise. The mixture was stirred for 2 h and concentrated to give 257.HCl (1.80 g, 98%). Data of 257.HCl: C7H13NO2.HCl (143.2, free base). 1H-NMR (DMSO-d6): 9.79 (br. s, 1H), 9.40 (br. s, 1H), 5.94 (m, 1H), 5.38 (qd, J=1.6, 17.3, 1H), 5.28 (qd, J=1.4, 10.5, 1H), 4.85 (m, 2H), 4.41 (q, J ca. 6.8, 1H), 2.55 (s, 3H), 1.48 (d, J=7.2, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With copper(l) iodide; caesium carbonate; In dimethyl sulfoxide; N,N-dimethyl-formamide; at 160℃; for 0.75h;Microwave irradiation; | Step 1 Synthesis of N-(3-cyanophenyl)-methyl-L-alanine 3-Iodobenzonitrile (916 mg, 4.00 mmol), N-methyl-L-alanine (618 mg, 6.00 mmol), cesium carbonate (1.95 g, 6.00 mmol) and copper iodide (76 mg, 0.4 mmol) were suspended in a mixed solvent of DMF (3.2 mL) and DMSO (0.8 mL). A microwave was irradiated thereon in a tightly-sealed container while stirring at 160 C. for 45 min, and the reaction solution was poured into 1M sodium hydroxide solution (100 mL) and the mixture was washed with dichloromethane. To the aqueous phase was added 3N hydrochloric acid up to about pH3, and the mixture was extracted with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel chromatography (dichloromethane:methanol) to give the title compound. yield: 660 mg (3.23 mmol) yield: 81% MS (ESI, m/z) 205 [M+H]+ 1H-NMR (CDCl3, 300 MHz) delta1.55 (d, 3H, J=7.2 Hz), 2.93 (s, 3H), 4.51 (q, 1H, J=7.2 Hz), 6.70-7.05 (m, 3H), 7.27-7.33 (m, 1H). |
[ 56857-47-7 ]
(S)-2-((Carboxymethyl)amino)propanoic acid
Similarity: 0.96
[ 2812-31-9 ]
(S)-2-(Dimethylamino)propanoic acid
Similarity: 0.93
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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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