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COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 13515-95-2 ]

CAS No. :	13515-95-2	MDL No. :	MFCD03658918
Formula :	C₇H₁₇ClN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	196.68	Pubchem ID :	-
Synonyms :

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Application In Synthesis of [ 13515-95-2 ]

* 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 [ 13515-95-2 ]
Downstream synthetic route of [ 13515-95-2 ]

[ 13515-95-2 ] Synthesis Path-Upstream 1~2

1
[ 13515-95-2 ]
[ 28957-33-7 ]

Reference： [1] Patent: US2002/151546, 2002, A1,

2
[ 13515-95-2 ]
[ 26081-03-8 ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: With sodium methylate In methanol at 20℃; for 4 h; Inert atmosphere; Reflux Stage #2: With hydrogenchloride In ethanol	L-Lysine hydrochloride (100.0 g, 547 mmol) dissolved inMeOH (1200 mL) was stirred for 30 min at 0 C under Ar. Thionyl chloride (80 mL, 1.10 mol) was addeddropwise over 20 min at 0 C. The solution was stirred for 1 h at room temperature, and refluxed forovernight. After removal of the solvent in vacuo, the crude product was recrystallized from MeOH to givemethyl L-lysinate dihydrochloride (124.1 g, yield 97percent). Methyl L-lysinate dihydrochloride (60.0 g, 257mmol) dissolved in MeOH (1200 mL) was stirred at room temperature under Ar. NaOMe (48.0 g, 889mmol) was added, and the solution was refluxed for 4 h. The mixture was hydrolyzed by addingammonium chloride (20.0 g), and the solution was filtered, and then the solvent was removed in vacuo.The residue was dissolved in dimethoxyethane (80 mL), and the solution was filtered, and then thesolvent was removed in vacuo. The residue was dissolved in EtOH (100 mL), and EtOH saturated withHCl (20 mL) was added to give the crude product. The crude product was recrystallized from MeOH togive (S)-3-aminozepan-2-one hydrochloride (5: 27.8 g, yield 66percent)

Reference： [1] Heterocycles, 2017, vol. 94, # 5, p. 964 - 978

Yield	Reaction Conditions	Operation in experiment
100%		Methanol (50 mL) was cooled down to 0 °C and thionyl chloride (100 mmol, 7.25 mL) was added dropwise. After stirring for ten minutes (S)-lysine (50.9 mmol, 7.31 g) was added portionwise and the reaction mixture was stirred for further ten minutes at 0 °C. Afterwards the mixture was heated to reflux for three hours. The reaction mixture was cooled down to room temperature and the solvent was removed under reduced pressure. After drying under vacuum (S)-lysine methyl ester dihydrochloride (50.9 mmol, 11.9 g, quant.) was obtained as white solid.1H-NMR (600 MHz, D2O): delta (ppm) = 1.27-1.41 (m, 2 H), 1.60 (td, J = 7.2 Hz,J = 15.5 Hz, 2 H), 1.75-1.81 (m, 1 H), 1.84-1.90 (m, 1 H), 2.84 (t, J = 7.7 Hz,2 H), 3.68 (s, 3 H), 4.00 (t, J = 6.5 Hz, 1 H).13C-NMR (91 MHz, D2O): delta (ppm) = 22.1 (CH2), 26.9 (CH2), 29.9 (CH2), 39.7 (CH2),53.3 (CH3), 54.2 (CH), 171.2 (Cq).
87%	With hydrogenchloride;	L-lysine (a) (14.60 g, 100 mmol) was dissolved in 150 mL of MeOH, anhydrous HCl gas was added until the solution changed from clarification to turbidity. Then, the solvent was evaporated with the desired compound b (17.10 g, 87 percent yield) being recrystallized as white solid by ester. Mp: 200-203 °C.

Yield	Reaction Conditions	Operation in experiment
31.8%	With triethylamine; In ethyl acetate; at 20℃; for 2h;	Example-2 2,6-Bis-(2-benzyloxy-acetylamino)-hexanoic acid methyl ester To a mixture of L-<strong>[13515-95-2]lysine methyl ester dihydrochloride</strong> (50 grams, 214.4 mmol), triethylamine (131 grams, 1.294 moles) in ethyl acetate (750 mL) at room temperature was added benzyloxy acetyl chloride (120 grams, 650.4 mmol) drop wise. The mixture was further stirred at room temperature for 2 hours. The solids were filtered off. The organic phase was washed with 5percent sodium bicarbonate (2100 mL), water (2100 mL), dried over sodium sulphate and distilled. The crude 2 was purified by column chromatography on silica gel using Benzene: Ethyl acetate (9:1) to get pure 2 (30 grams, 31.8percent) as a white powder. M.p: 62-65° C. 1H NMR (CDCl3) delta 1.36 (m, 2H, CH2), 1.56 (m, 2H, CH2), 1.76 (m, 2H, CH2), 3.28 (m, 2H, CH2) 3.78 (s, 3H, Ester), 3.96 (m, 3H, CH2 and CH), 4.60 (m, 6H, CH2x3), 6.60 (bt, 1H, NH), 7.06 (bd, 1H, NH), 7.34 (m, 10H, Ar).

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;	Further reductive amination reactions according to the invention are shown in Figure 22. Reductive amination of 40 with L-<strong>[13515-95-2]lysine methyl ester dihydrochloride</strong> 43 in the presence of triethylamine yields L-lysine derivative 97. This compound features two iminosugar moieties, formed by reaction of both available amino functions of 43 with two equivalents of xylo-pentodiasdose 40. In order to prove the suitability of the applied method for the "conjugation" of amino acids other than lysine, Z-L-Ser-OMe 47 is used as amino acid component. Reductive amination with 40 furnishes compound 98 in 73% yield, indicating that reductive amination of the alpha-amino function of various amino acids with dicarbonyl sugars is generally possible.

Yield	Reaction Conditions	Operation in experiment
55%	With triethylamine;	Due to the versatility with which adamantyl amide analogues can be synthesized by combining the commercially available 1-adamantylcarbonyl chloride with amino-acid methyl and ethyl esters, a series of adamantyl amnide analogues was synthesized. The resulting methyl and ethyl esters in all but one case were readily converted to the corresponding acids by saponification with lithium hydroxide as shown in (Scheme30).

Yield	Reaction Conditions	Operation in experiment
73%		The above (2-[2-(2-azidoethoxy)ethoxy]ethoxy)acetic acid (13g, 46.9mol) was dissolved in dichloromethane (100ml). N-Hydroxysuccinimide (6.5g, 56.3mmol) and 1 -ethyl-3-(3- dimethylaminopropylcarbodiimide hydrochloride (10.8g, 56.3mmol) was added and the reaction mixture was standing for 1 hour. Diisopropylethylamine (39ml, 234mmol) and L-<strong>[13515-95-2]lysine methyl ester dihydrochloride</strong> (6.Og, 25.8mmol) were added and the reaction mixture was standing for 16 hours. The reaction mixture was diluted with dichloromethane (300ml), extracted with water (100ml), hydrochloride (2N, 2x100ml), water (100ml), 50percent saturated sodi- umhydrogencarbonate (100ml) and water (2x100ml). The organic phase was dried with magnesium sulphate, filtered and evaporated in vacuo, giving an oil, which was used without further purification. Yield: 1 1 g (73 percent). LCMS: m/z = 591 . 13C-NMR (CDCI3): (selected) delta = 172.48; 169.87; 169.84; 71 .093-70.02; 53.51 ; 52.34; 51 .35; 50.64; 38.48; 36.48; 31 .99; 31 .40; 29.13; 22.82.
73%		(S)-2,6-Bis-(2-{2-[2-(2-azidoethoxy)ethoxy]ethoxy}acetylamino)hexanoic acid methyl ester EPO <DP n="86"/>The above (2-[2-(2-azidoethoxy)ethoxy]ethoxy)acetic acid (13g, 46.9mol) was dissolved in dichloromethane (100ml). N-Hydroxysuccinimide (6.5g, 56.3mmol) and 1 -ethyl-3-(3- dimethylaminopropylcarbodiimide hydrochloride (10.8g, 56.3mmol) was added and the reaction mixture was standing for 1 hour. Diisopropylethylamine (39ml, 234mmol) and L- <strong>[13515-95-2]lysine methyl ester dihydrochloride</strong> (6.Og, 25.8mmol) were added and the reaction mixture was standing for 16 hours. The reaction mixture was diluted with dichloromethane (300ml), extracted with water (100ml), hydrochloride (2N, 2x100ml), water (100ml), 50percent saturated sodiumhydrogencarbonate (100ml) and water (2x100ml). The organic phase was dried with magnesium sulphate, filtered and evaporated in vacuo, giving an oil, which was used without further purification. Yield: 1 1 g (73 percent). LCMS: m/z = 591 . 13C-NMR (CDCI3): (selected) delta = 172.48; 169.87; 169.84; 71 .093-70.02; 53.51 ; 52.34; 51 .35; 50.64; 38.48; 36.48; 31 .99; 31 .40; 29.13; 22.82.

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; at 20℃; for 24h;Product distribution / selectivity;	To a suspension of L-<strong>[13515-95-2]lysine methyl ester dihydrochloride</strong> (1.00 g,4.29 mmol) in 10 ml_ of methanol was added 1.22 ml_ (8.16 mmol) of 1 ,8- diazabicyclo[5.4.0]undec-7-ene. A solution of GDL (373 mg, 2.14 mmol) in2 mL of methanol was added dropwise to the resulting homogeneous solution. After the reaction had stirred at room temperature for 1 day, evaporation of solvent under vacuum and examination by 1H NMR showed the product to contain a 45:1 ratio of lysine acylated on the epsilon-amine versus the alpha-amine group. 1H NMR (500 MHz, DMSO-d6) delta 7.82 (t, J = 5.7 Hz, 1 H), 7.59 (t, J = 5.8 Hz, 1 H), 3.97 (d, J = 3.7 Hz, 1 H), 3.91 (d, J = 6.4 Hz, 1H), 3.85 (t, J = 3.4 Hz, 1 H), 3.66 (dd, J = 2.9, 6.3 Hz, 1H), 3.59 (s, 6H), 3.27 (m, 2H), 3.04 (m, 4H), 1.53-1.26 (m, 12H). 13C NMR (126 MHz, DMSO-CZ6) delta 176.27 (2C), 173.30, 172.33, 73.53, 73.19, 71.73, 70.57, 53.98 (2C), 51.56 (2C), 38.33, 38.25, 34.34 (2C), 29.05, 28.96, 22.68, 22.66.
		To a solution of L-<strong>[13515-95-2]lysine methyl ester dihydrochloride</strong> (0.341 g, 1.46 mmol) in 5 mL of methanol was added a solution of sodium hydroxide (0.117 g, 2.93 mmol) in methanol (5 mL). After stirring at ambient temperature for 25 minutes, the mixture was filtered to remove insolubles, and a solution of GDL (0.127 g, 7.31 mmol) in methanol (5 mL) was added. The reaction stirred several days at ambient temperature, and EPO <DP n="26"/>solvent was removed under vacuum to give 0.296 g (75 percent yield). 1H NMR showed the product to contain a 17:1 ratio of lysine acylated on the epsilon- amine versus lysine acylated on the alpha-amine group.

Yield	Reaction Conditions	Operation in experiment
99.4%	In methanol;	Step A. Preparation of L-lysine methyl ester dihydrochloride. MeOH (J. Org. Chem. 44, 4841 (1979)) To a stirred suspension of L-lysine monohydrochloride (190.7 g, 1.08 mol) in MeOH (3 L) was added (via a cannula) trimethylsilylchloride (350 mL). The mixture quickly became clear and homogeneous. The solution was stirred at reflux for 3 h and then at room temperature for 2 h. The reaction flask was left overnight in a refrigerator cooled to -75° C. The large crystals obtained were filtered, washed with cold MeOH (100 mL) and dried in vacuo for 24 h at room temperature. L-lysine methyl ester dihydrochloride. MeOH (275.8 g) was obtained in 99.4percent yield. 1H NMR (DMSO-d6): delta1.36 (m, 1H), 1.45 (m, 1H), 1.58 (m, 2H), 1.81 (m,2H), 2.74 (br s, 2H), 3.11 (s, 3H), 3.72 (s, 3H), 3.94 (t, J=4.0, 1H), 8.12 (br s, 3H), 8.72 (br s, 3H).

Yield	Reaction Conditions	Operation in experiment
	With ammonium chloride; sodium methylate; In methanol; ethanol;	Step B. Preparation of L-alpha-amino-epsilon-caprolactam hydrochloride(J. Org. Chem. 44, 4841 (1979)) Sodium methylate 58.73 g (1 mole) was dissolved in cold MeOH (1 L). About one half of this solution was cannulated into a solution of L-<strong>[13515-95-2]lysine methyl ester dihydrochloride</strong>. MeOH (132.5 g, 0.5 mole) in 1 L MeOH. The suspension was allowed to warm and dissolved. The remainder sodium methylate was added with concurrent apparition of NaCl. The mixture was then allowed to reflux for 4 h, after which 5 g of NH4Cl was added. The solution then sat at RT for 18 h and was filtered through celite. Evaporation of the MeOH resulted in a thick opaque syrup. The excess NaCl was removed by redissolving the mixture in boiling glyme (100 mL, 2*), filtering through celite and evaporating in vacuo. The resulting clear oil was taken up in ethanol and acidified with 12 N HCl. Cooling gave a mass of fine white needles which were filtered and dried in vacuo to yield 69.71 g, 85percent of the title compound. MP 301-306° C. [alpha]d=-24.8 (c=3.4, 1N HCl). 1H NMR (DMSO-d6): delta1.17 (q, J=12.6, 1H), 1.45 (q, J=12.6, 1H), 1.58 (q, J=12.6, 1H), 1.71 (d, J=12.6, 1H), 1.86 (d, J=12.6, 1H), 1.94 (d, J=12.6, 1H), 3.03 (m, 1H), 3.15 (m, 1H), 4.03 (d, J=12.6, 1H), 8.12 (br s, 1H),8.22 (br s, 3H). 13C NMR (DMSO-d6): delta28.2, 29.7, 29.9, 41.6, 53.4, 173.2. LC-MS: 129.1 (M+H)+, 99percent pure.

Yield	Reaction Conditions	Operation in experiment
		Example 5 Preparation of L-Lysine methyl ester-HA (formula XXIV)-Sodium hyaluronate (100 mg, 0.25 mmol) and L-lysine methyl ester dihydrochloride (1.748 g, 7.5 mmol) was dissolved in H2O (40 ml, 2.5 mg/ml HA). The pH was adjusted to 6.5 and HOBT (169 mg, 1.25 mmol) predissolved in a 1:1 mixture of water and DMSO (1 ml) and EDC (240 mg, 1.25 mmol) was added and the reaction mixture was stirred overnight. The pH was subsequently adjusted to 7.0 with 1M NaOH and NaCl added to produce a 5percent w/v solution. HA was precipitated by addition of three volume equivalents of ethanol. The precipitate was redissolved in H2O at a concentration of approximately 5 mg/ml and the precipitation repeated twice. The purified product was freeze dried and kept at 4° C. under N2. See FIG. 3Cfor NMR data of the product.

Yield	Reaction Conditions	Operation in experiment
	In water;	The resulting filter cake was then dried by airflow at 50° C. for 10 hours to obtain 197.0 g of L-lysine methyl ester dihydrochloride having a purity of 96.3percent and containing 1.5percent of L-lysine hydrochloride and 0.2percent of water. The yield of the product based on the additional L-lysine hydrochloride was 98.4percent. The filtrate, containing 31.0 g (as lysine) of lysine methyl ester hydrochloride and lysine hydrochloride, was used again in the esterification reaction.

Yield	Reaction Conditions	Operation in experiment
98%	With benzotriazol-1-ol; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20℃; for 24.25h;	LysOMe. 2EtaC1 (1.43 g, 6 mmol) was dissolved in DMF (45 mL) with the DIEA (2.35 g, 18 mmol), and then the HOBT (2.25 g, 14 mmol) was added. After 5 minutes ZLys(Z)OPFP (12.5 g, 21 mmol) in DCM (30 mL) was added at 0 0C for 10 minutes. The mixture was stirred for 24 h at RT under N2. After concentration under vacuum the mixture was dissolved in DCM (50 mL) washed with NaHCO3 (2x150 mL), water (2x150 mL) and then dried over NaSO4. The solvent was removed, and the mixture was precipitated in ether EPO <DP n="258"/>to lead a pure white compound 5.72 g (98percent).1H NMR (CDCl3): delta 1.35-1.79 (m, 18, CH2- CH2); 2.87 (m, 1, CH2-NH); 3.13 (m, 4, CH2-NH); 3.40 (m, 1, CH2-NH); 3.63 (s, 3, CH3); 4.16 (m, 1, CH-NEta); 4.34 (m, 1, CH-NEta); 4.38 (m, 1, CH-NEta); 4.88-5.02 (4 x s, 8, CH2- O); 5.13 (m, 1, CH2-NH); 5.28 (m, 1, CH2-NH); 5.94 (d, I5 CEta-NH); 6.25 (d, 1, CEta-NH); 6.88 (m, 1, CEta2-NH);7.19-7.27 (m, 20, arom CH). 7.43 (d, 1, CEta-NH). FAB MS: 953.4 m/z (MH+) (theory. 952.4 m/z (M+)). Elemental analysis: (theory: C, 64.27; H, 6.77; Nu, 8.82; O, 20.14) found C, 63.98; H, 6.79; Nu, 8.81; O, 20.39.

Yield	Reaction Conditions	Operation in experiment
11 g (73%)	With N-ethyl-N,N-diisopropylamine; In dichloromethane;	Example 14 (S)-2,6-Bis-(2-{2-[2-(2-azidoethoxy)ethoxy]ethoxy}acetylamino)hexanoic acid methyl ester The above (2-[2-(2-azidoethoxy)ethoxy]ethoxy)acetic acid (13 g, 46.9 mol) was dissolved in dichloromethane (100 ml). N-Hydroxysuccinimide (6.5 g, 56.3 mmol) and 1-ethyl-3-(3-dimethylaminopropylcarbodiimide hydrochloride (10.8 g, 56.3 mmol) was added and the reaction mixture was standing for 1 hour. Diisopropylethylamine (39 ml, 234 mmol) and L-<strong>[13515-95-2]lysine methyl ester dihydrochloride</strong> (6.0 g, 25.8 mmol) were added and the reaction mixture was standing for 16 hours. The reaction mixture was diluted with dichloromethane (300 ml), extracted with water (100 ml), hydrochloride (2N, 2100 ml), water (100 ml), 50percent saturated sodiumhydrogencarbonate (100 ml) and water (2100 ml). The organic phase was dried with magnesium sulphate, filtered and evaporated in vacuo, giving an oil, which was used without further purification. Yield: 11 g (73percent). LCMS: m/z=591. 13C-NMR (CDCl3): (selected) delta=172.48; 169.87; 169.84; 71.093-70.02; 53.51; 52.34; 51.35; 50.64; 38.48; 36.48; 31.99; 31.40; 29.13; 22.82.

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H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
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

[ CAS No. 13515-95-2 ] {[proInfo.proName]}

Quality Control of [ 13515-95-2 ]

Related Doc. of [ 13515-95-2 ]

Product Details of [ 13515-95-2 ]

Safety of [ 13515-95-2 ]

Application In Synthesis of [ 13515-95-2 ]

[ 13515-95-2 ] Synthesis Path-Upstream 1~2

[ 13515-95-2 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry