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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Glycine Methyl Ester HCl is a glycine derivative, commonly used in biochemical research and drug synthesis.
Synonyms: Methyl 2-aminoacetate hydrochloride
4.5
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 5680-79-5 |
Formula : | C3H8ClNO2 |
M.W : | 125.55 |
SMILES Code : | NCC(OC)=O.[H]Cl |
Synonyms : |
Methyl 2-aminoacetate hydrochloride
|
MDL No. : | MFCD00012870 |
InChI Key : | COQRGFWWJBEXRC-UHFFFAOYSA-N |
Pubchem ID : | 122755 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
74% | With triethylamine; In dimethyl sulfoxide; at 140℃; for 0.5h;Microwave irradiation; | Example-88 (6-Methyl-5-nitro-2-pyridin-2-ylamino)-butionic methyl ester 6-chloro-3-nitro-2-picoline (600 mg, 3.5 mmol) was coupled with glycine methyl ester hydrochloride (880 mg, 7 mmol), triethylamine (1.5 ml, 10.5 mmol) in DMSO 3 mL at 140 °C for 30 min in microwave (Parameters : high absorbance, fixed holding time, pre- stirring 25 seconds). The crude mixture was treated with a saturated aqueous solution of NH4Cl. The aqueous solution of was extracted with EtOAc, washed with water and brine. The crude product was purified on a silica column with CH2Cl2-MeOH as mobile phase. This gave 39 mg (51percent) of 580 mg (74percent) of (6-methyl-5-nitro-2-pyridin-2-ylarcino)- budonic methyl ester as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; | Elemental Analysis Found C, 56.5; H, 4.8; N, 12.4; C21 H21 ClN4 O3 S requires C, 56.7; H, 4.8; N, 12.6%. The N-(6-chloronaphth-2-ylsulphonyl)glycine used as a starting material was obtained as follows: Triethylamine (0.278 ml) was added to a stirred mixture of 6-chloronaphth-2-ylsulphonyl chloride (0.522 g), glycine methyl ester hydrochloride (0.251 g) and methylene chloride (10 ml) and the mixture was stirred at ambient temperature for 1 hour. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4) and evaporated. The residue was recrystallized from methanol to give methyl N-(6-chloronaphth-2-ylsulphonyl)glycine (0.46 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | Example 1: Synthesis of [l-(l,4-dimethyl-lH-indol-3-ylmethyl)-2,4-dioxo-l,4-dihydro-2H- pyrido[3,4-rf]pyrimidin-3-yl]-acetic acid; To a solution of lOOmg of 3-amino-isonicotinic acid in pyridine (2.5 mL) is added 117 mg of l,l'-carbonyldiimidazole and the mixture is stirred for 20 min at 55 0C. Then the mixture is cooled to room temperature and 91 mg of glycine methylester hydrochloride is added and the resulting mixture is stirred for 30 min at 55 0C and 1 h at room temperature. Then the solvent is removed under vaccum and the residue is purified by flash chromatography on silica gel to give 100 mg (66 percent) of [(3-amino-pyridine-4-carbonyl)-amino]-acetic acid methyl ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.11 To a solution of H-Gly-OMe HC1 (40 mg, 0.32mmol, 1 eq) in DMF (3 mL) was added sequentially Boc-N-Me-Hydroxyphenylglycine (122 mg, 1.35 eq), HOBT (43 mg, 1 eq), EDC (67 mg, 1.1 eq) and TEA (49 muEpsilon, 1.1 eq). The solution was allowed to stir overnight then dilute NaHC03(aq) and EtOAc, the aqueous phase was extracted 3x with EtOAc and the combined organic fractions were washed with 5% citric acid (pH - 3), water and brine. The organics were dried over sodium sulfate, concentrated then the crude was taken on directly without further purification. The crude residue (113 mg) was taken up in acetone (3.5 mL), treated with Mel (139 muEpsilon, 7 eq) and K2CO3 (221 mg, 5 eq) and heated at reflux in a sealed vial overnight. The reaction was then allowed to warm to room temperature, the volatiles were blown off and water and EtOAc were added. The aqueous layer was extracted 3x with EtOAc and the combined organic layers were dried over sodium sulfate and concentrated. Column chromatography (3% MeOH in DCM) yielded the product (64.3 mg, 55% yield over two steps). lH NMR (CDC13, 500 MHz) delta (ppm) 7.27 (d, J = 8.5 Hz, 2H), 6.89 (d, J = 8.5 Hz, 2H), 6.49 (br s, 1H), 5.84 (br s, 1H), 4.09-4.08 (m, 2H), 3.80 (s, 3H), 3.75 (s, 3H), 2.71 (s, 3H), 1.47 (s, 9H) 13C NMR (CDC13, 500 MHz) delta (ppm) 170.6, 170.2, 159.6, 130.6, 127.2, 114.1, 80.6, 55.3, 52.4, 41.3, 31.5, 32.1 , 28.4. MS (ESI) m/z 389.2 (M + Na+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93 mg | With triethylamine; In ethanol; at 80℃; | A) methyl N-(5-fluoro-3-nitropyridin-2-yl)glycinate To a solution of methyl glycinate hydrochloride (1.39 g) and <strong>[136888-21-6]2-chloro-5-fluoro-3-nitropyridine</strong> (2.00 g) in ethanol (35.9 mL) was added triethylamine (3.79 mL). The reaction mixture was stirred overnight at 80C, and the solvent was evaporated under reduced pressure. The residue was diluted with ethyl acetate, and the mixture was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (93.0 mg). MS (API+): [M+H]+230.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11.1 g | With triethylamine; In ethanol; for 20.0h;Reflux; | A) methyl N-(5-iodo-3-nitropyridin-2-yl)glycinate To a solution of <strong>[426463-05-0]2-chloro-5-iodo-3-nitropyridine</strong> (12.0 g) in ethanol (200 mL) were added methyl glycinate hydrochloride (10.6 g) and triethylamine (11.8 mL) at room temperature. The reaction mixture was heated at reflux for 20 hr, and the solvent was evaporated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was crystallized from hexane/ethyl acetate to give the title compound (11.1 g). MS (API+): [M+H]+ 338.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.4% | With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In N,N-dimethyl acetamide; at 25℃; for 10h;Green chemistry; | 3,5-dichloro-2-pyridine carboxylic acid (20.5g, 0 . 107mol) and 1 - (3-dimethylamino-propyl) - 3-ethyl carbodiimide (26.5g, 0 . 17mol) dissolved in N, N-dimethyl acetamide (130 ml), by adding glycine methyl ester hydrochloride (17.4g, 0 . 139mol), dropping triethylamine (54.0g, 0 . 53mol), reaction mixture 25 C stirring reaction 10 hours, TLC confirmed board after the reaction, the reaction solution by the spin vaporization of concentrated to dry, by adding dilute hydrochloric acid is adjusted to neutral, by adding ethyl acetate extraction, magnesium sulfate drying, concentrating to dry the spin vaporization, methanol is recrystallized, shall be N-(3,5- two chloropyridine -2-carbonyl) glycine methyl ester, kind of white solid (24.0g), yield 85.4% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Glycine methyl ester hydrochloride (925 mg, 7.37 mmol, 1.1 eq) was added to a solution of triethylamine (1.07 mL, 8.04 mmol, 1.2 eq) in toluene (20 mL). The reaction mixture was stirred for 30 minutes on 3 A molecular sieves. Then <strong>[54221-96-4]6-methoxy-2-pyridinecarboxaldehyde</strong> (0.92 g, 6.70 mmol, 1.0 eq) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered, diluted with toluene and cooled to 0° C., and used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | General procedure: The corresponding 4-(Diphenylphosphino)benzoic acid (1 mmol) was dissolved in dichloromethane (50 mL). HOBt*H2O (1 mmol), TBTU(1 mmol) and DIPEA (0.5 mL, 4 mmol) were added and the mixture was left stirring at room temperature. After 1 h methyl ester (1 mmol) was added and the mixture was left stirring for the indicated period. After that, the reaction mixture was washed with NaHCO3 (3×50 mL, sat.aq.) and subjected to flash chromatography (hexane/EtOAc). |
Tags: Glycine Methyl Ester HCl | Methyl 2-aminoacetate hydrochloride | C-protective Amino Acid | Amino Acids | 5680-79-5
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