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CAS No. : | 2483-62-7 | MDL No. : | MFCD03840864 |
Formula : | C5H11NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 117.15 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 | UN#: | N/A |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
With methanol; hydroxylamine at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.3% | With thionyl chloride; at 0℃; for 2h;Inert atmosphere; Reflux; | Step 1 Methyl (2S)-2-aminobutanoate; (2S)-2-Aminobutanoic acid 41a (21.56 g, 0.21 mol) was dissolved in 120 mL of methanol. The reaction solution was cooled down to 0C in an ice-water bath, added dropwise with thionyl chloride (30.5 mL, 0.42 mol) with stirring. Upon the completion of the addition, the reaction mixture was heated to reflux for 2 hours, then cooled down to room temperature. The reaction solution was concentrated under reduced pressure to obtain the title compound methyl (2S)-2-aminobutanoate 41b (31.87 g, yield: 99.3%) as a white solid. |
99.3% | With thionyl chloride; at 0℃; for 2h;Reflux; | Step 1 Methyl (2S)-2-aminobutanoate (2S)-2-Aminobutanoic acid 41a (21.56 g, 0.21 mol) was dissolved in 120 mL of methanol. The reaction solution was cooled down to 0 C. in an ice-water bath, added dropwise with thionyl chloride (30.5 mL, 0.42 mol) with stirring. Upon the completion of the addition, the reaction mixture was heated to reflux for 2 hours, then cooled down to room temperature. The reaction solution was concentrated under reduced pressure to obtain the title compound methyl (2S)-2-aminobutanoate 41b (31.87 g, yield: 99.3%) as a white solid. |
93% | With thionyl chloride; at 0 - 20℃; for 40h; | Example C: (S)-2-amino-butyric acid methyl esterNH2 HCIA solution of (S)-2-amino-butyric acid (1.0 g, 9.7 mmol) in methanol (20 mL) is cooled to O0C and thionyl chloride (1.0 mL, 13.7 mmol) is added dropwise. The reaction mixture is stirred at ambient temperature for 40 hours is then concentrated to provide the title compound (1.38 g, 93%). |
1.12 g | With thionyl chloride; for 1.5h;Reflux; | Weigh the compound 1 (lg, 9.96 mmol) in lOmL methanol and slowly add thionyl chloride (1.48 ml, 20.36 mmol) at 0 C under ice-water bath and reflux at 65 C for 1.5 h. After the reaction, The The remaining oil was stirred with 10 ml of methyl t-butyl ether for 0.5 h. The resulting colorless crystals were filtered, washed with ether and dried in vacuo overnight to give the title compound 2 (1.12 g, quant.) As a colorless semi-solid crystal, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.7% | With thionyl chloride at -30 - 20℃; for 21h; Inert atmosphere; | |
With thionyl chloride | ||
With thionyl chloride at 0 - 20℃; |
With thionyl chloride at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanol; ammonia; at -10 - 20℃; for 6 - 7h; | Example 1 : Preparation of (S)-2-aminobutanamide; Methyl (S)-2-aminobutyric acid ester (220 g) was dissolved in methanol (1200 ml). The reaction mixture was cooled to -5 to - 100C and ammonia gas was passed for about 4 hours. The temperature was slowly raised to 200C in about 2 to 3 hours and ammonium sulfate (120 g) was added at 20 to 25C. The reaction mixture was stirred at 20 to 25C for 2 to 3 days. The reaction mixture was filtered through celite bed and washed with methanol (100 ml). The combined filtrate was concentrated to get crude product, which was recrystallized from methanol-ethyl acetate to get the title compound. Yield: 138 g Purity (HPLC): 91.36% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sodium acetate; sodium tris(acetoxy)borohydride; In dichloromethane; at 20℃; for 16h; | Compound 2 (lg, 8.54 mmol), cyclopentanone (582 uL, 6.58 mmol)And dissolved in 11 ml of methylene chloride. 0 ice water bath under the conditions of adding anhydrous sodium acetate(539 mg, 6.58 mmol) and triacetoxyborohydride (2.03 g, 9.57 mmol). At room temperature for 16h, add 15ml 20% sodium bicarbonate solution, dichloromethane extraction 3 times, the organic phase, washed with water, anhydrous magnesium sulfate drying, filtration, distillation under reduced pressure to obtain a pale yellow oil compound 4 (1.18g, Yield 97%). |
77.1% | Step 2 Methyl (2S)-2-(cyclopentylamino)butanoate; Methyl (2S)-2-aminobutanoate 41b (18.74 g, 0.12 mol) was dissolved in 280 mL of dichloromethane. The reaction solution was cooled down to 0C in an ice-water bath followed by the addition of sodium acetate (5 g, 0.061 mol), cyclopentanone (10.78 g, 0.13 mol) and sodium triacetoxyborohydride (31 g, 0.16 mol) successively. The reaction solution was heated to room temperature and stirred for 4 hours. The reaction solution was poured into 150 mL of water, added dropwise with saturated sodium carbonate solution to adjust pH to 11 to 12 and seperated. The aqueous phase was extracted with dichloromethane (150mL×2). The combined organic phase was washed with saturated brine (100mL×2), then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to obtain the title compound methyl (2S)-2-(cyclopentylamino)butanoate 41c (17.42 g, yield: 77.1%) as a light yellow oil. MS m/z (ESI): 186.1 [M+1] | |
77.1% | With sodium acetate; sodium tris(acetoxy)borohydride; In dichloromethane; at 0 - 20℃; for 4h; | Step 2 Methyl (2S)-2-(cyclopentylamino)butanoate Methyl (2S)-2-aminobutanoate 41b (18.74 g, 0.12 mol) was dissolved in 280 mL of dichloromethane. The reaction solution was cooled down to 0 C. in an ice-water bath followed by the addition of sodium acetate (5 g, 0.061 mol), cyclopentanone (10.78 g, 0.13 mol) and sodium triacetoxyborohydride (31 g, 0.16 mol) successively. The reaction solution was heated to room temperature and stirred for 4 hours. The reaction solution was poured into 150 mL of water, added dropwise with saturated sodium carbonate solution to adjust pH to 11 to 12 and separated. The aqueous phase was extracted with dichloromethane (150 mL*2). The combined organic phase was washed with saturated brine (100 mL*2), then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to obtain the title compound methyl (2S)-2-(cyclopentylamino)butanoate 41c (17.42 g, yield: 77.1%) as a light yellow oil.MS m/z (ESI): 186.1 [M+1] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.7% | Step 1 Methyl (2S)-2-(isopropylamino)butanoate; (2S)-2-Aminobutanoate 41b (13.14 g, 85.52 mmol) was dissolved in 200 mL of dichloromethane. The reaction solution was cooled down to 0C in an ice-water bath followed by the addition of sodium acetate (3.51 g, 42.76 mmol), acetone (5.96 g, 0.10 mol) and sodium triacetoxyborohydride (21.75 g, 0.10 mol) successively. The reaction solution was heated to room temperature and stirred for 4 hours. The resulting solution was added with 100 mL of water, added dropwise with saturated sodium carbonate solution to adjust pH to 11 to 12 and separated. The aqueous phase was extracted with dichloromethane (150 mL×2). The combined organic phase was washed with saturated brine (100 mL×2), then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to obtain methyl (2S)-2-(isopropylamino)butanoate 43a (10.85 g, yield: 79.7%) as a light yellow oil. MS m/z (ESI): 160.2 [M+1] | |
79.7% | With sodium acetate; sodium tris(acetoxy)borohydride; In dichloromethane; at 0 - 20℃; for 4h; | Step 1 Methyl (2S)-2-(isopropylamino)butanoate (2S)-2-Aminobutanoate 41b (13.14 g, 85.52 mmol) was dissolved in 200 mL of dichloromethane. The reaction solution was cooled down to 0 C. in an ice-water bath followed by the addition of sodium acetate (3.51 g, 42.76 mmol), acetone (5.96 g, 0.10 mol) and sodium triacetoxyborohydride (21.75 g, 0.10 mol) successively. The reaction solution was heated to room temperature and stirred for 4 hours. The resulting solution was added with 100 mL of water, added dropwise with saturated sodium carbonate solution to adjust pH to 11 to 12 and separated. The aqueous phase was extracted with dichloromethane (150 mL*2). The combined organic phase was washed with saturated brine (100 mL*2), then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to obtain methyl (2S)-2-(isopropylamino)butanoate 43a (10.85 g, yield: 79.7%) as a light yellow oil. MS m/z (ESI): 160.2 [M+1] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium acetate; sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | General procedure: The respective O-protected oxycarbamoylheptanoic acid 23 (1 equivalent) suspended or dissolved in THF (3mLpermmol) was treated with N-methylmorpholine and stirred at r.t. for 10min. Then isobutyl chloroformate (1 equivalent) was added at -10C and stirring was continued at this temperature for 15min. The amino acid ester (1 equivalent) and again N-methylmorpholine (2 equivalents) were added and stirring was continued at -10C for 10min and at r.t. for one more hour. The mixture was poured into 2N HCl (50mL) and extracted with ethyl acetate (2×25mL) and the combined organic layer was washed with 5% bicarbonate solution and brine. After drying over MgSO4 the solvent was removed in vacuo and the product was purified by column chromatography (silica gel, ethyl acetate). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | General procedure: To a solution of alanine methyl ester hydrochloride (3.00 g, 21.6 mmol) in CH2Cl2(120 mL) was added NMM (6.19 mL, 45.5 mmol) and methanesulphonyl chloride (1.67mL, 21.6 mmol). The reaction was stirred at room temperature for 20h. Thereaction was quenched upon addition of 1 N HCl (120 mL) and extracted with CH2Cl2(2 x 100 mL). The combined organic extracts were dried over Na2SO4and concentrated under vacuum. The residue was dissolved in DMF (100 mL) andadded K2CO3 (5.94 g, 44.0 mmol) and 4-bromobenzyl bromide(6.00 g, 24.0 mmol). The reaction was stirred at 40 C for 6h. The reaction wascooled to room temperature, diluted with water (400 mL) and extracted withEtOAc (2 x 200 mL). The combined organic extracts were washed with 5% LiCl (aq.Solution., 2 x 300 mL) and brine (300 mL), dried over Na2SO4and concentrated under vacuum. The residue was purified by columnchromatography (silica gel) using 0 to 70% EtOAc/hexanes to afford 2 a clear yellow oil (5.56 g, 73%); 1H-NMR(400 MHz, CDCl3) delta 7.45 (dt, J= 8.5, 2.0 Hz, 2H), 7.29 (dt, J =8.5, 2.0 Hz, 2H), 4.68 (q, J = 8.0Hz, 1H), 4.59 (d, J = 16.0 Hz, 1H), 4.25 (d, J= 16.0 Hz, 1H), 3.73 (s, 3H), 2.95 (s, 3H), 1.32 (d, J = 8.0 Hz, 3H); 13C-NMR (100 MHz, CDCl3) delta 172.1,136.8, 131.6, 129.5, 121.6, 56.2, 52.5, 48.8, 39.8, 17.5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 20℃; for 3h; | Step 3: HATU (1.12 mmol, 1.2 eq.) and DIPEA (3.7 mmol, 4.0 eq.) were added sequentially to a stirred mixture of the product from Step 2 (0.93 mmol) and the appropriate protected amino acid (0.93 mmol) in DMF (5 mL) at 0 C. followed by slow warming to rt and stirring at this temperature for 3 h. The mixture was then partitioned between EtOAc and 10% HCl aqueous solution. The organic phase was separated and washed with saturated NaHCO3 and brine, dried over MgSO4, filtrated and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with an increasing proportion of MeOH in CH2Cl2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.8% | The compound 1 (11.7g, 0. lmol) was added to 100mL of isopropanol, cooled to 0 ~ 5 C, ammonia to saturation, the reaction at room temperature 36h, the reaction was completed, concentrated to dryness, was added 50mL isopropanol , The introduction of ammonia lh, reaction at room temperature 2h, filtered, concentrated to dryness, 100mL isopropanol was added dropwise hydrochloric acid isopropanol solution, the drop was completed, crystal lh, filtered, washed with isopropanol, dried in vacuo to give Compound 2 (12.9 g, molar yield 92.8 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.5% | With triethylamine; In tert-butyl alcohol; at 90℃; for 30h;Inert atmosphere; | Methyl L-2-aminobutyrate (A2, 5.85 g, 50 mmol),Compound B1 (10.32g, 40.6mmol) and triethylamine (6.81g, 67.4mmol) were dissolved in tert-butanol (40mL), protected with N2, and refluxed at 90 C for 30h.The reaction was monitored by HPLC until B1 disappeared. The reaction solution is cooled to ambient temperature,The solvent was distilled off under reduced pressure, washed with water, filtered, and then dried and evaporated to yield11.23 g, yield 82.5% (HPLC: 97.2%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride | 22 Intermediate 62: methyl 2-(4-bromo-3-fluoro-2-nitro-anilino)butanoate Intermediate 62: methyl 2-(4-bromo-3-fluoro-2-nitro-anilino)butanoate DIPEA (165 ml, 942.91 mmol) was added slowly to a stirred solution of 1-bromo-2,4-difluoro-3-nitro-benzene (intermediate 35) (74.8 g, 314.30 mmol) and methyl 2-aminobutanoate, HCl (48.3 g, 314.30 mmol) in DMF (733 mL) and the resulting solution was stirred at rt for 18 hours. DMF was removed on rocket evaporator, diluted with water and extracted with ethyl acetate. After concentration the crude material was purified by flash silica chromatography, elution gradient 0 to 70% EtOAc in hexanes. Product fractions were concentrated under reduced pressure to afford methyl 2-(4-bromo-3-fluoro-2-nitro-anilino)butanoate (intermediate 62) (49.4 g, 47%) as a red solid. 1H NMR (500 MHz, DMSO-d6) 0.82-0.98 (3H, m), 1.77-1.93 (2H, m), 3.70 (3H, d), 4.38-4.54 (1H, m), 6.77 (1H, br d), 7.28 (1H, br d), 7.64-7.80 (1H, t); m/z (ES+) [M+H]+=335. |
Tags: 2483-62-7 synthesis path| 2483-62-7 SDS| 2483-62-7 COA| 2483-62-7 purity| 2483-62-7 application| 2483-62-7 NMR| 2483-62-7 COA| 2483-62-7 structure
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