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Product Details of [ 5680-79-5 ]

CAS No. :5680-79-5 MDL No. :MFCD00012870
Formula : C3H8ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :COQRGFWWJBEXRC-UHFFFAOYSA-N
M.W : 125.55 Pubchem ID :122755
Synonyms :
Methyl 2-aminoacetate hydrochloride
Chemical Name :H-Gly-OMe.HCl

Calculated chemistry of [ 5680-79-5 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 27.49
TPSA : 52.32 Ų

Pharmacokinetics

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) : -7.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.01
Log Po/w (WLOGP) : -0.08
Log Po/w (MLOGP) : -0.39
Log Po/w (SILICOS-IT) : -0.72
Consensus Log Po/w : -0.24

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.49
Solubility : 40.4 mg/ml ; 0.322 mol/l
Class : Very soluble
Log S (Ali) : -0.66
Solubility : 27.4 mg/ml ; 0.219 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.1
Solubility : 157.0 mg/ml ; 1.25 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 5680-79-5 ]

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:

Application In Synthesis of [ 5680-79-5 ]

* 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.

  • Upstream synthesis route of [ 5680-79-5 ]
  • Downstream synthetic route of [ 5680-79-5 ]

[ 5680-79-5 ] Synthesis Path-Upstream   1~34

  • 1
  • [ 5680-79-5 ]
  • [ 1611-78-5 ]
  • [ 1193-62-0 ]
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  • 2
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  • [ 5680-79-5 ]
  • [ 4774-22-5 ]
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  • 3
  • [ 5680-79-5 ]
  • [ 79-07-2 ]
  • [ 4774-22-5 ]
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  • 4
  • [ 5680-79-5 ]
  • [ 74-89-5 ]
  • [ 22356-89-4 ]
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  • 5
  • [ 5680-79-5 ]
  • [ 124-40-3 ]
  • [ 22356-89-4 ]
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  • 6
  • [ 5781-53-3 ]
  • [ 5680-79-5 ]
  • [ 89464-63-1 ]
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[6] Patent: WO2005/87767, 2005, A1, . Location in patent: Page/Page column 25-26
  • 7
  • [ 553-90-2 ]
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  • [ 89464-63-1 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In methanol 1) N-Methoxycarbonylmethyloxamic acid methyl ester N-Methoxycarbonylmethyloxamic acid methyl ester (19.86 g, quantitative) was obtained as an oily product according to the method of E. Menta, et al., (J. Heterocyclic Chem., 1995, 32, 1693), using glycine methyl ester hydrochloride (12.59 g), dimethyl oxalate (23.65 g), triethylamine (14.0 mL) and methanol (110 mL). 1H-NMR(400MHz, CDCl3)δ: 3.79(3H, s), 3.92(3H, s), 4.14(2H, d, J=5.6Hz), 7.55(1H, br). ESI-MSm/z: 176(M+H)+.
Reference: [1] Patent: EP1785418, 2007, A1, . Location in patent: Page/Page column 66
  • 8
  • [ 123-91-1 ]
  • [ 24424-99-5 ]
  • [ 5680-79-5 ]
  • [ 42492-57-9 ]
Reference: [1] Patent: US5747535, 1998, A,
  • 9
  • [ 123-91-1 ]
  • [ 24424-99-5 ]
  • [ 5680-79-5 ]
  • [ 42492-57-9 ]
Reference: [1] Patent: EP739886, 1996, A2,
  • 10
  • [ 24424-99-5 ]
  • [ 5680-79-5 ]
  • [ 6926-09-6 ]
YieldReaction ConditionsOperation in experiment
73%
Stage #1: With sodium hydrogencarbonate In acetonitrile at 0 - 20℃; for 21 h; Inert atmosphere
Stage #2: With hydrazine hydrate In ethanol at 20℃; for 24 h;
The compound 2-aminoacetic acid methyl ester hydrochloride was added(28.1 g, 224 mmol) and sodium bicarbonate (36.4 g, 433 mmol)Suspended in acetonitrile (400 mL)And then di-tert-butyl dicarbonate was added to the stirred reaction solution under the reaction of 0 ° C under nitrogen(45 mL, 200 mmol). The mixture was stirred at room temperature for 21 hours and then concentrated under reduced pressure. The residue was diluted with H2O (40 mL) to give The mixture was extracted with DCM (50 mL x 3). The combined organic phases were washed with saturated brine (50 mL), dried over anhydrous sodium sulfate, Concentrated under reduced pressure to give a white solid which was used directly in the next step.The white solid was dissolved in ethanol (100 mL) and then at room temperature, Hydrazine hydrate (27 mL) was added to the solution, and the resulting mixture was stirred at room temperature for 24 hours and then concentrated under reduced pressure. The residue was diluted with H? O (50 mL) and the resulting mixtureDCM (100 mL x 3). The combined organic phases were washed with saturated brine (60 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure A white solid was obtained which was used directly in the next step (31 g, 73percent) without further purification.
Reference: [1] Patent: CN105924434, 2016, A, . Location in patent: Paragraph 0883; 0884; 0885; 0886
  • 11
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  • [ 3321-03-7 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 34, p. 11980 - 11983
  • 12
  • [ 5680-79-5 ]
  • [ 98-59-9 ]
  • [ 2645-02-5 ]
YieldReaction ConditionsOperation in experiment
78% With sodium carbonate In dichloromethane at 20℃; Cooling with ice General procedure: Syntheses of G(2–4) and P(2–4): General experimental procedure is as follows: Glycine or L-phenyl alanine derivative (as HCl salt) (10 mmol) and Na2CO3 (2.1 g, 20 mmol) were dissolved in anhydrous dichloromethane (50 mL) and cooled in an ice bath before tosyl chloride (1.9 g, 10 mmol) was added. The resultant reaction mixture was stirred overnight at room temperature. After the reaction, more solvent was added and the residue was washed sequentially with 0.1 M HCl, saturated NaHCO3 and brine. Organic portion was dried with Na2SO4 and concentrated in vacuo to give crude product. The product was purified by column chromatography on silica with hexane and EtOAc (1:1). Compound G2: Yield 78percent as white solid. 1H NMR (400 MHz,CDCl3): δ 7.74 (d, J= 8.3 Hz, 2H, ArH), 7.31 (d, J= 8.3 Hz, 2H, ArH), 5.04 (t, J= 5.1 Hz, 1H, –NH–), 3.78 (d, J= 5.1 Hz, 2H, –CH2–), 3.64 (s, 3H, –OCH3), 2.42 (s, 3H, –CH3) ppm. 13C NMR (100 MHz, CDCl3): δ 169.4, 144.0, 136.3, 129.9, 127.4, 52.7, 44.2, 21.7 ppm. Anal.Calcd. [C10H13NO4S]: C, 49.37; H, 5.39; N, 5.76; S, 13.18. Found:C, 50.63; H, 5.09; N, 5.36; S, 12.87.
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  • 13
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  • [ 100-52-7 ]
  • [ 53386-64-4 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 12, p. 6210 - 6222
[2] Patent: WO2017/59191, 2017, A1, . Location in patent: Paragraph 001095
  • 14
  • [ 5680-79-5 ]
  • [ 1668-10-6 ]
Reference: [1] Journal fur Praktische Chemie - Chemiker - Zeitung, 1996, vol. 338, # 3, p. 251 - 256
  • 15
  • [ 67-56-1 ]
  • [ 56-40-6 ]
  • [ 5680-79-5 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: for 1 h; Cooling with ice
Stage #2: at 20 - 66℃; for 6.5 h;
(2)
Preparation of glycine methyl ester hydrochloride
Under ice bath, 100 ml round-bottom flask was added with 60 ml of methanol, and then slowly added with 4 ml of SOCl2 through constant pressure dropping funnel (with a drying tube on the top), and NaOH solution was used to absorb exhaust.
After stirring for 1 h, 8 mmol of glycine was added and stirred at room temperature for 30 min, and then refluxed at 66° C. for 6 h.
The reaction was tracked by TLC until the raw materials disappeared, with a solution of 2percent ninhydrin in ethanol as chromogenic reagent.
The solvent was evaporated out to obtain glycine methyl ester hydrochloride. Yield: 100percent.
99% at -5 - 20℃; for 3 h; Inert atmosphere Under N2 dryCH3OH (100 mL) was cooled down to -5 °C and SOCl2 (21 mL,0.3mol) was added dropwise. Glycine (7.5 g, 0.1mol) was added to this solutionand stirring was continued at rt for 3 h. The solvent and gaseous reactionproducts were removed under reduced pressure to obtain the pure product ascolorless crystals, mp 180 °C (ref. 175-178 oC)9, yield12.4 g (99 percent). C3H8ClNO2 (125.5 g / mol).FT-IR (neat): v (cm-1) =2879 (s, vC-H aliphatic), 1744 (s, vC=O ester), 1582/1496(m, vN-H). 1H NMR(400MHz, CD3OD): δ (ppm) = 3.84 (s, 3H, CO2CH3),3.89 (s, 2H, CH2). The signal for NH3+-protonsis not seen in the 1H NMR-spectrum. 13C NMR (101MHz, CD3OD):δ (ppm) = 40.2 (1C, CH2), 53.5 (1C, CO2CH3), 168.8 (1C, C=O).
98% at -5 - 20℃; General procedure: A suspension of L-amino acid (50mmol) in methanol (50mL) was stirred under ice cold conditions. Thionyl chloride (5mL) was slowly dropped to the solution at−5°C. Then, the mixture was allowed to slowly warm to room temperature while being stirred. The reaction was monitored by TLC (N-butanol: water: acetic acid=4:1:1). When the reaction was completed, the solvent was evaporated under reduced pressure to afford the crude product, which was recrystallized from methanol/ether to give a white solid.
96% at 0 - 20℃; To a solution of SOCl2(2.33mL; 3.2 10-2 mol) in MeOH at 0°C, the glycine (2g, 2.6610-2mol) was added. The mixture was stirred at rt overnight. Reaction mixture was evaporated under vacuum. The residue was dissolved in MeOH and evaporated again under vacuum. This procedure was repeated three times. The residue was recrystallized in a mixture of MeOH and Et2O to provide a fluffy powder (2.27g, 96percent). IR (ATR): 3109,3012, 2882, 2687, 2635, 1743, 1584, 1557 cm-1. 1H NMR(300 MHz, DMSO D6) δ ppm 8.64(s, 3H), 3.76 (s, 2H), 3.72 (s, 3H). 13C NMR (75MHz, DMSO D6) δ 167.9,52.4, 39.3.
90% at 20℃; for 24 h; Sealed tube Amino acid is placed into a 50 ml one-port flask and added with 2.0 eq. TMSC1 dropwise before adding 5 mL of dry methanol as the solvent. The reaction mixture is sealed and allowed to react at room temperature with stirring for 24 h. Upon completion of the reaction, the solvent is evaporated and methanol (3X10 mL) is further added to co-evaporate the residual hydrochloride. Ethyl ether is then added to the oily product obtained after the evaporation and a white solid is precipitated and further recrystallized with methanol-ethyl ether.
90% at 20℃; for 24 h; Sealed tube Example 4 [0068] Synthesis of amino acid methyl ester hydrochloride is described as follows. Amino acid is placed into a 50 ml one-port flask and added with 2.0 eq. TMSCl dropwise before adding 5 mL of dry methanol as the solvent. The reaction mixture is sealed and allowed to react at room temperature with stirring for 24 h. Upon completion of the reaction, the solvent is evaporated and methanol (3×10 mL) is further added to co-evaporate the residual hydrochloride. Ethyl ether is then added to the oily product obtained after the evaporation and a white solid is precipitated and further recrystallized with methanol-ethyl ether. Experimental data for the products are shown in the table below.
90% for 2 h; Reflux General procedure: 26.2 g (200 mmol) trans-4-hydroxy-L-proline (1) in methanol(300 ml) was treated with dry hydrogen chloride until homogeneous.The solution was heated to the reflux temperature for 2 h and concentrated in vacuo. Upon cooling, the product was crystallizedfrom the solvent, collected by filtration, washed with acetoneand ether, and dried to yield trans-4-hydroxy-L-proline methylesterhydrochloride (2) as white crystal (32.7 g, 90percent), mp 159–162 C.
90.68%
Stage #1: at -5 - 5℃; for 1 h;
Stage #2: at 70℃; for 5 h;
Control the temperature of -5 ~ 5 ° C, acetyl chloride 23.56g drop by drop to no waterMethanol 60ml, the drip after the incubation reaction lh, divided into two batches of glycine 7.51g, add the system temperature to 70 ° C reaction 5h, minusPressure to remove the excess solvent,The residue was further added with acetone 30 ml for 5 h,filter,The filter cake was dried in vacuo to give 11.39 g of glycine methyl ester hydrochloride in a yield of 90.68percent and a melting point of 174-176 ° C.
81% at 0 - 20℃; for 16 h; To a stirred solution of 2-aminoacetic acid 8-1 (2 g, 26.64 mmol) in MeOH (20 mL) was added thionyl chloride (5.8 mL, 79.92 mmol) at 0 °C, and stirred at RT for 16 hr. The solvents were evaporated under reduced pressure and the crude residue was purified by washings with pentane/ether to afford 9-10A (2.7 g, 21.6 mmol, 81percent yield) as a brown solid.
4.93 g at 65 - 70℃; for 1.25 h; In the first step, glycine methyl ester hydrochloride is prepared by weighing 3 g of glycine, adding 150mL of anhydrous methanol, heating in an oil bath at 65 ° C to 70 ° C, continuously feeding dry Hcl gas,completely dissolving glycine in about 60 min, and continuing to pass Hcl gas. After 15 min, the reactionwas stopped, concentrated under reduced pressure, and the residue was stirred with acetone to givewhite crystals 4.93g

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YieldReaction ConditionsOperation in experiment
99.5% With thionyl chloride In methanol at -10℃; for 0.166667 h; IIIa the compound (3g, 40mmol) dissolved in MeOH (30 ml) in, salt bath cooling to -10 °C, stirring slowly dripping SOCl2(29 ml, 400mmol), reaction after the end of the dropping 10 min, to remove salt bath, the reaction at room temperature overnight, TLC detection reaction, concentrating under reduced pressure, then adding 20mLCH2Cl2, repeatedly two times concentrated under reduced pressure, the solvent turns on lathe does, drying, the obtained product 5g, the yield is 99.5percent, product without purification, used directly in the next reaction.
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YieldReaction ConditionsOperation in experiment
100% at 20℃; for 24 h; To a stirring solution of glycine methyl ester hydrochloride (17.49 g, 139 mmol) in dry dichloromethane (150 mL) under N2 at room temperature was added diphenylimine (25.00 g, 137 mmol) in one portion. The reaction mixture was stirred for 24 h, during which time ammonium chloride precipitated. Water (20 mL) was added and the layers were separated. The organic layer was washed with saturated Na2CO3 solution (2 x 20 mL) and brine (20 mL). The organic layer was dried (Na2SO4), filtered and concentrated by rotary evaporation to give ~ 35 g of a thick light brown syrup (99 percent pure) in ~ 100 percent yield. This was taken on to the next reaction without further purification.
100% at 20℃; for 24 h; To a stirring solution of methyl glycine ester hydrochloride (17.49 g, 139 mmol) in dry dichloromethane (150 mL) under N2 at room temperature was added diphenylimine (25.00 g, 137 mmol) in one portion. The reaction mixture was stirred for 24 h, during which time ammonium chloride precipitated. Water (20 mL) was added and the layers were separated. The organic layer was washed with saturated Na2C03 solution (2 x 20 mL) and brine (20 mL). The organic layer was dried (Na2SC>4), filtered and concentrated by rotary evaporation to give ~35 g of a thick light brown syrup (99percent pure) in ~ 100percent yield. This was taken on to the next reaction without further purification.
92% at 20℃; for 24 h; Benzophenone imine (50.0 g, 0.276 mol) was added in one batch to a solution of glycine methyl ester hydrochloride (39.4 g, 0.314 mol) in 300 mL dichloromethane under stirring, and the resulting reaction solution was stirred at room temperature for 1 day.
The resulting solid was removed by filtration, and the filtrate was washed sequentially with water, sodium carbonate solution and saturated brine, and was concentrated by evaporation to give methyl 2-((diphenylmethylene)amino)acetate (64.2 g) as an oily product, which was solidified after being cooled, and used directly for next step. Yield: 92percent. 1H-NMR (400 MHz, CDCl3): δ= 7.66 (2H, m), 7.45 (4H, m), 7.35 (2H, m), 7.17 (2H, m), 4.22 (2H, s), 3.74 (3H, s).
81% at 25℃; for 24 h; Inert atmosphere To a stirred suspension containing 5.00 g (39.9 mmol) of glycine methyl ester hydrochloride in 20 mL of anhydrous CH2Cl2 was added dropwise 6.70 mL (7.20 g, 39.9 mmol) of benzophenone imine.The milky white mixture was stirred at 25 °C for 24 h under an argon atmosphere. The reaction mixture was filtered and concentrated under diminished pressure. The crude product was crystallized from ether–hexanes to afford 3 as colorless crystals: yield 8.20 g (81percent); silica gel TLC Rf 0.22 (1:9 ethyl acetate−hexanes); 1H NMR (CDCl3) δ 3.73 (s, 3H), 4.21 (s, 2H), 7.15-7.18(m, 2H), 7.30-7.45 (m, 6H) and 7.63-7.66 (m, 2H); 13C NMR (CDCl3)δ 52.0, 55.6, 127.6, 128.1, 128.69,128.75, 128.83, 130.5, 135.9, 139.2, 171.1 and 171.9; mass spectrum (APCI), m/z 254.1182 (M + H)+ (C16H16NO2 requires m/z 254.1181).
81% at 25℃; for 24 h; Inert atmosphere [0067] Methyl 2-(diphenylmethyleneamino)acetate (41). To a stirred suspension containing 5.00 g (39.9 mmol) of glycine methyl ester hydrochloride (40) in 20 mL of anhydrous CH2CI2 was added 6.70 mL (7.20 g, 39.9 mmol) of benzophenone imine drop wise. The white mixture was stirred at 25 °C for 24 h under argon atmosphere. The reaction mixture was filtered and concentrated under diminished pressure. [0068] The crude product was crystallized from ether-hexanes to afford 41 as white crystals; yield 8.20 g (81percent); silica gel TLC R{ 0.22 (1 :9 ethyl acetate-hexanes); XH NMR (CDCI3) δ 3.73 (s, 3H), 4.21 (s, 2H), 7.15-7.18 (m, 2H), 7.30-7.45 (m, 6H) and 7.63-7.66 (m, 2H); 1 C NMR (CDCI3) δ 52.0, 55.6, 127.6, 128.05, 128.69, 128.75, 128.83, 130.5, 135.9, 139.2, 171.1 and 171.9; mass spectrum (APCI), m/z 254.1182 (M + H)+ (Ci6Hi6N02 requires m/z 254.1181).

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