[ CAS No. 15366-32-2 ] {[proInfo.proName]}

Name: 15366-32-2|Ethyl 2-(1-methylguanidino)acetate hydrochloride|95%
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SKU: A104706
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Quality Control of [ 15366-32-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 15366-32-2 ]

SDS Specification

Alternatived Products of [ 15366-32-2 ]

Product Details of [ 15366-32-2 ]

CAS No. :	15366-32-2	MDL No. :	MFCD08704792
Formula :	C₆H₁₄ClN₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SZZVKHCNEZPXOL-UHFFFAOYSA-N
M.W :	195.65	Pubchem ID :	25114309
Synonyms :

Calculated chemistry of [ 15366-32-2 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	5
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	48.4
TPSA :	79.41 Å²

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) :	-7.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.33
Log Po/w (WLOGP) :	0.18
Log Po/w (MLOGP) :	0.18
Log Po/w (SILICOS-IT) :	-1.0
Consensus Log Po/w :	-0.06

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.93
Solubility :	22.9 mg/ml ; 0.117 mol/l
Class :	Very soluble
Log S (Ali) :	-1.56
Solubility :	5.37 mg/ml ; 0.0275 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.21
Solubility :	120.0 mg/ml ; 0.614 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.14

Safety of [ 15366-32-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 15366-32-2 ]

* 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 [ 15366-32-2 ]
Downstream synthetic route of [ 15366-32-2 ]

[ 15366-32-2 ] Synthesis Path-Upstream 1~4

1
[ 64-17-5 ]
[ 57-00-1 ]
[ 15366-32-2 ]

Yield	Reaction Conditions	Operation in experiment
73%	at 0 - 60℃; for 0.75 h;	Example 12Ethyl[[[amino](imino)methyl](methyl)amino]acetate (24); Phosphorochloridic acid (2.0-2.5 equivalents to creatine) was added dropwise to a suspension of creatine in 10 mL of ethanol at 0° C. The reaction mixture was stirred for 15 min at 0° C. and the temperature then raised to 60° C. and stirred for 30 min. The reaction mixture was then cooled to provide 1.7 g of the hydrochloride salt of title compound (24) (73percent yield) as a white solid. ¹H NMR (CD₃OD, 400 MHz): δ 4.20-4.30 (m, 4H), 3.16(s, 3H, creatinine NCH₃), 3.08 (s, 3H, CBE NCH₃), 1.31 (d, J=6.8 Hz), (CBE/creatinine=9:1).
54%	at 37℃; for 20 h; Acidic conditions	Optimization experiments were performed by varying certain parameters of the reaction scheme in Example 1, as described below. A 1.5 mole equivalent of acetyl chloride was added dropwise to anhydrous ethanol to generate the acidified ethanol. Creatine monohydrate was added to the acidified ethanol at a ratio of 1 g:6 ml of ethanol and the reaction medium was heated to 37° C. for 20 hours. The reaction medium was then allowed to cool to 30° C. prior to filtration and the product (filter cake) was washed with ethanol chilled to 0° C. The amount of ethanol used in the wash was on a 1:1 w/v (g/ml) basis with the quantity of creatine monohydrate employed as the starting material. This reaction scheme yielded an 83 to 86percent conversion of creatine monohydrate to CEE HCl. [0044] A. Length of Reaction Time [0045] Shortening the reaction time from 20 hours to 10-12 hours resulted in a decrease in the conversion of creatine monohydrate to CEE HCl to about 76 to 83percent. Increasing the reaction time to greater than 20 hours resulted in no significant increase in the conversion of creatine monohydrate to CEE HCl. Such longer reaction times, however, did result in the increased formation of the undesirable product creatinine HCl. [0046] B. Temperature at Filtration [0047] After heating the reaction medium to 37° C. for 20 hours, the reaction medium was cooled to various temperatures prior to filtration. The results of these experiments are summarized in Table 1. [TABLE-US-00001] TABLE 1 Temperature Product Product At Filtration Purity Yield 30° C. 99percent 54percent 25° C. 95percent 66percent 6° C. 94percent 79percent [0048] Cooling the filtrate to 6° C. resulted in significantly greater yields compared to either 25° C. or 30° C., but with a relatively slight loss of purity. In each of these experiments, the primary impurity found in the reaction product was creatine HCl. [0049] C. Ratio of Acetyl Chloride to Creatine Monohydrate [0050] The ratio of acetyl chloride to creatine monohydrate was varied to optimize the production of CEE HCl while minimizing the formation of the undesired product creatinine HCl. The amount of acetyl chloride employed was varied between 1.3 and 2.0 mole equivalents and the results of the experiments are summarized in Table 2. [TABLE-US-00002] TABLE 2 Mole equivalents of Product Product acetyl chloride Conversion Purity Yield 1.3 74percent 99percent 37percent 1.4 84percent 98percent 48percent 1.5 83-86percent 99percent 54percent 1.6 86percent 99percent 57percent 2.0 83percent 93percent 63percent [0051] The only impurity present in the final solid reaction product was creatine HCl when 1.3 to 1.6 mole equivalents of acetyl chloride were employed. Creatinine HCl was the only impurity identified when 2.0 equivalents were employed. These results indicate that 1.5 to 1.6 equivalents of acetyl chloride may be optimal as these conditions produced the greatest conversion and yield of the desired product with a high degree of purity. Higher amounts of acetyl chloride, such as greater than 2.0 mole equivalents, are less desirable despite the higher yields because of the greater production of the undesired creatinine HCl reaction byproduct. [0052] D. Composition of Starting Ethanol [0053] The composition of the starting ethanol to which the acetyl chloride is added was varied between a 100:0 and 80:20 ratio (v/v) of ethanol (EtOH) to ethyl acetate (EtOAc). The results of these experiments are presented in Table 3. [TABLE-US-00003] TABLE 3 EtOH:EtOAc Product Product (v/v) Conversion Purity Yield 100:0 83-86percent 99percent 54percent 95:5 88percent 96percent 65percent 90:10 87percent 93percent 64percent 80:20 84percent 93percent 64percent [0054] These data indicate that the 95:5 EtOH:EtOAc ratio (v/v) may be preferred because the increase in yield likely outweighs the slight loss in purity. One notable disadvantage with using larger amounts of EtOAc is that the reaction impurities consisted of about a 3:1 molar ratio of creatinine HCl:creatine HCl. Filtering the reaction mixture at a slightly higher temperature would improve the purity of the isolated CEE HCl, but as noted hereinabove (see part B) such an increase in temperature may result in a concomitant decrease in yield. [0055] Notably, all of the acetyl chloride added to the ethanol is also converted to EtOAc. Therefore the actual ratio of EtOH:EtOAc at the time of creatine monohydrate addition is different than the starting material. [0056] A number of literature and patent references are cited in the foregoing application in order to more fully describe the state of the art to which this invention pertains. The entire disclosure of each of these citations is incorporated by reference herein. [0057] While certain embodiments of the present invention have been described and/or specifically exemplified above, various other embodiments will be apparent to those skilled in the art from the foregoing disclosure. The present invention is, therefore, not limited to such embodiments, but is capable of considerable variation and modification without departing from the scope of the following claims.

Reference： [1] Patent: US2007/281909, 2007, A1, . Location in patent: Page/Page column 53-54
[2] Patent: US2005/49428, 2005, A1, . Location in patent: Page/Page column 3-4
[3] Biochemische Zeitschrift, 1925, vol. 156, p. 186
[4] Journal of Biological Chemistry, 1922, vol. 54, p. 672
[5] Patent: US2006/67880, 2006, A1, . Location in patent: Page/Page column 1
[6] Patent: US9833427, 2017, B2, . Location in patent: Sheet 8/18

2
[ 57-00-1 ]
[ 15366-32-2 ]

Reference： [1] Patent: US2005/49428, 2005, A1, . Location in patent: Page/Page column 3

3
[ 64-17-5 ]
[ 57-00-1 ]
[ 15366-32-2 ]
[ 141-78-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: at 35 - 60℃; Stage #2: at 35 - 50℃; for 2 - 8 h;	Synthesis of Creatine Ethyl Ester Hydrochloride by Acid-Catalyzed Esterification of Creatine Monohyrdate [0039] A 1.5 molar equivalent of acetyl chloride was added dropwise to either anhydrous ethanol protected by a calcium chloride drying tube with constant stirring. The acetyl chloride was added at such a rate so as to prevent the temperature of the acidified solvent from exceeding 60° C. [0040] The temperature of the acidified ethanol was then allowed to decline to about 35 to 40° C. When the acidified ethanol reached the lower temperatures, creatine monohydrate was added in one portion in the ratio of 1 g of creatine monohydrate to 6 to 10 ml of acidified ethanol. The resultant reaction was stirred for 2 to 8 hours at about 40 to 50° C. [0041] The temperature of the reaction mixture was then allowed to cool to about room temperature with constant stirring. White crystalline creatine ethyl ester hydrochloride (CEE HCl) was collected by vacuum filtration and washed with approximately 1 ml of ice cold ethanol per 1 g of CEE HCl product. After the removal of most of the solvent by vacuum filtration, the CEE HCl was removed from the filter and then allowed to dry in a fume hood. [0042] The yield of CEE HCl from this method was 74percent, but a total yield of about 80 to 92percent (i.e. conversion) is obtainable when the CEE HCl remaining in the filtrate or mother liquor following the initial isolation of CEE HCl is considered. Additionally, the reaction product is 94 to 100percent CEE HCl, with any impurities consisting of hydrochlorides of creatine and creatinine.
37%	Stage #2: at 37℃; for 10 - 20 h;	Optimization experiments were performed by varying certain parameters of the reaction scheme in Example 1, as described below. A 1.5 mole equivalent of acetyl chloride was added dropwise to anhydrous ethanol to generate the acidified ethanol. Creatine monohydrate was added to the acidified ethanol at a ratio of 1 g:6 ml of ethanol and the reaction medium was heated to 37° C. for 20 hours. The reaction medium was then allowed to cool to 30° C. prior to filtration and the product (filter cake) was washed with ethanol chilled to 0° C. The amount of ethanol used in the wash was on a 1:1 w/v (g/ml) basis with the quantity of creatine monohydrate employed as the starting material. This reaction scheme yielded an 83 to 86percent conversion of creatine monohydrate to CEE HCl. [0044] A. Length of Reaction Time [0045] Shortening the reaction time from 20 hours to 10-12 hours resulted in a decrease in the conversion of creatine monohydrate to CEE HCl to about 76 to 83percent. Increasing the reaction time to greater than 20 hours resulted in no significant increase in the conversion of creatine monohydrate to CEE HCl. Such longer reaction times, however, did result in the increased formation of the undesirable product creatinine HCl. [0046] B. Temperature at Filtration [0047] After heating the reaction medium to 37° C. for 20 hours, the reaction medium was cooled to various temperatures prior to filtration. The results of these experiments are summarized in Table 1. [TABLE-US-00001] TABLE 1 Temperature Product Product At Filtration Purity Yield 30° C. 99percent 54percent 25° C. 95percent 66percent 6° C. 94percent 79percent [0048] Cooling the filtrate to 6° C. resulted in significantly greater yields compared to either 25° C. or 30° C., but with a relatively slight loss of purity. In each of these experiments, the primary impurity found in the reaction product was creatine HCl. [0049] C. Ratio of Acetyl Chloride to Creatine Monohydrate [0050] The ratio of acetyl chloride to creatine monohydrate was varied to optimize the production of CEE HCl while minimizing the formation of the undesired product creatinine HCl. The amount of acetyl chloride employed was varied between 1.3 and 2.0 mole equivalents and the results of the experiments are summarized in Table 2. [TABLE-US-00002] TABLE 2 Mole equivalents of Product Product acetyl chloride Conversion Purity Yield 1.3 74percent 99percent 37percent 1.4 84percent 98percent 48percent 1.5 83-86percent 99percent 54percent 1.6 86percent 99percent 57percent 2.0 83percent 93percent 63percent [0051] The only impurity present in the final solid reaction product was creatine HCl when 1.3 to 1.6 mole equivalents of acetyl chloride were employed. Creatinine HCl was the only impurity identified when 2.0 equivalents were employed. These results indicate that 1.5 to 1.6 equivalents of acetyl chloride may be optimal as these conditions produced the greatest conversion and yield of the desired product with a high degree of purity. Higher amounts of acetyl chloride, such as greater than 2.0 mole equivalents, are less desirable despite the higher yields because of the greater production of the undesired creatinine HCl reaction byproduct. [0052] D. Composition of Starting Ethanol [0053] The composition of the starting ethanol to which the acetyl chloride is added was varied between a 100:0 and 80:20 ratio (v/v) of ethanol (EtOH) to ethyl acetate (EtOAc). The results of these experiments are presented in Table 3. [TABLE-US-00003] TABLE 3 EtOH:EtOAc Product Product (v/v) Conversion Purity Yield 100:0 83-86percent 99percent 54percent 95:5 88percent 96percent 65percent 90:10 87percent 93percent 64percent 80:20 84percent 93percent 64percent [0054] These data indicate that the 95:5 EtOH:EtOAc ratio (v/v) may be preferred because the increase in yield likely outweighs the slight loss in purity. One notable disadvantage with using larger amounts of EtOAc is that the reaction impurities consisted of about a 3:1 molar ratio of creatinine HCl:creatine HCl. Filtering the reaction mixture at a slightly higher temperature would improve the purity of the isolated CEE HCl, but as noted hereinabove (see part B) such an increase in temperature may result in a concomitant decrease in yield. [0055] Notably, all of the acetyl chloride added to the ethanol is also converted to EtOAc. Therefore the actual ratio of EtOH:EtOAc at the time of creatine monohydrate addition is different than the starting material. [0056] A number of literature and patent references are cited in the foregoing application in order to more fully describe the state of the art to which this invention pertains. The entire disclosure of each of these citations is incorporated by reference herein. [0057] While certain embodiments of the present invention have been described and/or specifically exemplified above, various other embodiments will be apparent to those skilled in the art from the foregoing disclosure. The present invention is, therefore, not limited to such embodiments, but is capable of considerable variation and modification without departing from the scope of the following claims.

Reference： [1] Patent: US2005/49428, 2005, A1, . Location in patent: Page/Page column 3
[2] Patent: US2005/49428, 2005, A1, . Location in patent: Page/Page column 3-4

4
[ 60-27-5 ]
[ 64-17-5 ]
[ 15366-32-2 ]

Reference： [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 5173 - 5181

[ 15366-32-2 ] Synthesis Path-Downstream 1~10

1
[ 15366-32-2 ]
[ 109-89-7 ]
[ 71-43-2 ]
[ 60-27-5 ]

Reference： [1]Biochemische Zeitschrift,1925,vol. 156,p. 186

2
[ 64-17-5 ]
[ 57-00-1 ]
[ 15366-32-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	With phosgene; dmap; at 10℃; for 0.5h;Sealed tube;	1000 g of ethanol was sequentially added to a 2000 mL flask equipped with a stirring device.1.0 g 4-dimethylaminopyridine, 100 g creatine monohydrate, stir and cool to 10 C,Start to add 100g of phosgene (produced by the reaction of concentrated sulfuric acid and carbon tetrachloride, slowly added after low temperature condensation),After the completion of the dropwise addition, the reaction was carried out for 30 minutes. After filtration, it is dried in a hot air oven at 100 C.Obtained 117 g of a white solid (based on anhydrous creatine,The yield was 89%).
73%	With chlorophosphonic acid; at 0 - 60℃; for 0.75h;	Example 12Ethyl[[[amino](imino)methyl](methyl)amino]acetate (24); Phosphorochloridic acid (2.0-2.5 equivalents to creatine) was added dropwise to a suspension of creatine in 10 mL of ethanol at 0 C. The reaction mixture was stirred for 15 min at 0 C. and the temperature then raised to 60 C. and stirred for 30 min. The reaction mixture was then cooled to provide 1.7 g of the hydrochloride salt of title compound (24) (73% yield) as a white solid. 1H NMR (CD3OD, 400 MHz): delta 4.20-4.30 (m, 4H), 3.16(s, 3H, creatinine NCH3), 3.08 (s, 3H, CBE NCH3), 1.31 (d, J=6.8 Hz), (CBE/creatinine=9:1).
54%	at 37℃; for 20h;Acidic conditions;Product distribution / selectivity;	Optimization experiments were performed by varying certain parameters of the reaction scheme in Example 1, as described below. A 1.5 mole equivalent of acetyl chloride was added dropwise to anhydrous ethanol to generate the acidified ethanol. Creatine monohydrate was added to the acidified ethanol at a ratio of 1 g:6 ml of ethanol and the reaction medium was heated to 37 C. for 20 hours. The reaction medium was then allowed to cool to 30 C. prior to filtration and the product (filter cake) was washed with ethanol chilled to 0 C. The amount of ethanol used in the wash was on a 1:1 w/v (g/ml) basis with the quantity of creatine monohydrate employed as the starting material. This reaction scheme yielded an 83 to 86% conversion of creatine monohydrate to CEE HCl. [0044] A. Length of Reaction Time [0045] Shortening the reaction time from 20 hours to 10-12 hours resulted in a decrease in the conversion of creatine monohydrate to CEE HCl to about 76 to 83%. Increasing the reaction time to greater than 20 hours resulted in no significant increase in the conversion of creatine monohydrate to CEE HCl. Such longer reaction times, however, did result in the increased formation of the undesirable product creatinine HCl. [0046] B. Temperature at Filtration [0047] After heating the reaction medium to 37 C. for 20 hours, the reaction medium was cooled to various temperatures prior to filtration. The results of these experiments are summarized in Table 1. [TABLE-US-00001] TABLE 1 Temperature Product Product At Filtration Purity Yield 30 C. 99% 54% 25 C. 95% 66% 6 C. 94% 79% [0048] Cooling the filtrate to 6 C. resulted in significantly greater yields compared to either 25 C. or 30 C., but with a relatively slight loss of purity. In each of these experiments, the primary impurity found in the reaction product was creatine HCl. [0049] C. Ratio of Acetyl Chloride to Creatine Monohydrate [0050] The ratio of acetyl chloride to creatine monohydrate was varied to optimize the production of CEE HCl while minimizing the formation of the undesired product creatinine HCl. The amount of acetyl chloride employed was varied between 1.3 and 2.0 mole equivalents and the results of the experiments are summarized in Table 2. [TABLE-US-00002] TABLE 2 Mole equivalents of Product Product acetyl chloride Conversion Purity Yield 1.3 74% 99% 37% 1.4 84% 98% 48% 1.5 83-86% 99% 54% 1.6 86% 99% 57% 2.0 83% 93% 63% [0051] The only impurity present in the final solid reaction product was creatine HCl when 1.3 to 1.6 mole equivalents of acetyl chloride were employed. Creatinine HCl was the only impurity identified when 2.0 equivalents were employed. These results indicate that 1.5 to 1.6 equivalents of acetyl chloride may be optimal as these conditions produced the greatest conversion and yield of the desired product with a high degree of purity. Higher amounts of acetyl chloride, such as greater than 2.0 mole equivalents, are less desirable despite the higher yields because of the greater production of the undesired creatinine HCl reaction byproduct. [0052] D. Composition of Starting Ethanol [0053] The composition of the starting ethanol to which the acetyl chloride is added was varied between a 100:0 and 80:20 ratio (v/v) of ethanol (EtOH) to ethyl acetate (EtOAc). The results of these experiments are presented in Table 3. [TABLE-US-00003] TABLE 3 EtOH:EtOAc Product Product (v/v) Conversion Purity Yield 100:0 83-86% 99% 54% 95:5 88% 96% 65% 90:10 87% 93% 64% 80:20 84% 93% 64% [0054] These data indicate that the 95:5 EtOH:EtOAc ratio (v/v) may be preferred because the increase in yield likely outweighs the slight loss in purity. One notable disadvantage with using larger amounts of EtOAc is that the reaction impurities consisted of about a 3:1 molar ratio of creatinine HCl:creatine HCl. Filtering the reaction mixture at a slightly higher temperature would improve the purity of the isolated CEE HCl, but as noted hereinabove (see part B) such an increase in temperature may result in a concomitant decrease in yield. [0055] Notably, all of the acetyl chloride added to the ethanol is also converted to EtOAc. Therefore the actual ratio of EtOH:EtOAc at the time of creatine monohydrate addition is different than the starting material. [0056] A number of literature and patent references are cited in the foregoing application in order to more fully describe the state of the art to which this invention pertains. The entire disclosure of each of these citations is incorporated by reference herein. [0057] While certain embodiments of the present invention have been described and/or specifically exemplified above, various other embodiments will be apparent to those skilled in the art from the foregoing disclosure. The present invention is, therefore, not limited to such embodiments, but is capable of considerable variation and modification without departing from the scope of the following claims.

With acetyl chloride; In water; at 40℃;

A general procedure for the preparation of creatine ethyl ester hydrochloride will now be described. Two ml of anhydrous ethanol is diluted with 67 mul of a 9:1 mixture of ethanol and water and stirred under an Argon atmosphere. To the mixture is added acetyl chloride (164 mul, 2.30 mmol) and the solution stirred for 5 minutes. The solution is heated to 40 degrees C. and creatine (200 mg, 1.53 mmol) is added to the stirring mixture. The mixture is stirred overnight at 40 degrees C. The creatine ethyl ester hydrochloride is recovered by cooling the mixture to 0 degrees C., filtering the white precipitate and washing it with a minimum quantity of cold ethanol. The material can be stored under anhydrous conditions at -15 degrees C.

Reference： [1]Patent: CN108929249,2018,A .Location in patent: Paragraph 0012; 0029; 0031-0035
[2]Patent: US2007/281909,2007,A1 .Location in patent: Page/Page column 53-54
[3]Patent: US2005/49428,2005,A1 .Location in patent: Page/Page column 3-4
[4]Biochemische Zeitschrift,1925,vol. 156,p. 186
[5]Patent: US2006/67880,2006,A1 .Location in patent: Page/Page column 1
[6]Patent: US9833427,2017,B2 .Location in patent: Sheet 8/18

3
[ 15366-32-2 ]
by drying heating [ No CAS ]
[ 60-27-5 ]

Reference： [1]Journal of Biological Chemistry,1922,vol. 54,p. 672

4
[ 57-00-1 ]
[ 15366-32-2 ]

Yield	Reaction Conditions	Operation in experiment
48 - 63%	With hydrogenchloride;	Similar experiments performed with hydrogen chloride introduced directly from a gas cylinder led to yields of CEE HCl of only 48 to 63%.

Reference： [1]Patent: US2005/49428,2005,A1 .Location in patent: Page/Page column 3

Yield	Reaction Conditions	Operation in experiment
		Creatine ethyl ester hydrochloride 1H NMR(500 MHz, CDCl3) delta1.12(dq, J=6.0 Hz, J=1.0 Hz, 3H), 2.91, (s,3H), 4.10-4.11 (m, 4H).

6
[ 64-17-5 ]
[ 57-00-1 ]
[ 15366-32-2 ]
[ 141-78-6 ]

Yield	Reaction Conditions	Operation in experiment
80 - 92%		Synthesis of Creatine Ethyl Ester Hydrochloride by Acid-Catalyzed Esterification of Creatine Monohyrdate [0039] A 1.5 molar equivalent of acetyl chloride was added dropwise to either anhydrous ethanol protected by a calcium chloride drying tube with constant stirring. The acetyl chloride was added at such a rate so as to prevent the temperature of the acidified solvent from exceeding 60 C. [0040] The temperature of the acidified ethanol was then allowed to decline to about 35 to 40 C. When the acidified ethanol reached the lower temperatures, creatine monohydrate was added in one portion in the ratio of 1 g of creatine monohydrate to 6 to 10 ml of acidified ethanol. The resultant reaction was stirred for 2 to 8 hours at about 40 to 50 C. [0041] The temperature of the reaction mixture was then allowed to cool to about room temperature with constant stirring. White crystalline creatine ethyl ester hydrochloride (CEE HCl) was collected by vacuum filtration and washed with approximately 1 ml of ice cold ethanol per 1 g of CEE HCl product. After the removal of most of the solvent by vacuum filtration, the CEE HCl was removed from the filter and then allowed to dry in a fume hood. [0042] The yield of CEE HCl from this method was 74%, but a total yield of about 80 to 92% (i.e. conversion) is obtainable when the CEE HCl remaining in the filtrate or mother liquor following the initial isolation of CEE HCl is considered. Additionally, the reaction product is 94 to 100% CEE HCl, with any impurities consisting of hydrochlorides of creatine and creatinine.
37 - 79%		Optimization experiments were performed by varying certain parameters of the reaction scheme in Example 1, as described below. A 1.5 mole equivalent of acetyl chloride was added dropwise to anhydrous ethanol to generate the acidified ethanol. Creatine monohydrate was added to the acidified ethanol at a ratio of 1 g:6 ml of ethanol and the reaction medium was heated to 37 C. for 20 hours. The reaction medium was then allowed to cool to 30 C. prior to filtration and the product (filter cake) was washed with ethanol chilled to 0 C. The amount of ethanol used in the wash was on a 1:1 w/v (g/ml) basis with the quantity of creatine monohydrate employed as the starting material. This reaction scheme yielded an 83 to 86% conversion of creatine monohydrate to CEE HCl. [0044] A. Length of Reaction Time [0045] Shortening the reaction time from 20 hours to 10-12 hours resulted in a decrease in the conversion of creatine monohydrate to CEE HCl to about 76 to 83%. Increasing the reaction time to greater than 20 hours resulted in no significant increase in the conversion of creatine monohydrate to CEE HCl. Such longer reaction times, however, did result in the increased formation of the undesirable product creatinine HCl. [0046] B. Temperature at Filtration [0047] After heating the reaction medium to 37 C. for 20 hours, the reaction medium was cooled to various temperatures prior to filtration. The results of these experiments are summarized in Table 1. [TABLE-US-00001] TABLE 1 Temperature Product Product At Filtration Purity Yield 30 C. 99% 54% 25 C. 95% 66% 6 C. 94% 79% [0048] Cooling the filtrate to 6 C. resulted in significantly greater yields compared to either 25 C. or 30 C., but with a relatively slight loss of purity. In each of these experiments, the primary impurity found in the reaction product was creatine HCl. [0049] C. Ratio of Acetyl Chloride to Creatine Monohydrate [0050] The ratio of acetyl chloride to creatine monohydrate was varied to optimize the production of CEE HCl while minimizing the formation of the undesired product creatinine HCl. The amount of acetyl chloride employed was varied between 1.3 and 2.0 mole equivalents and the results of the experiments are summarized in Table 2. [TABLE-US-00002] TABLE 2 Mole equivalents of Product Product acetyl chloride Conversion Purity Yield 1.3 74% 99% 37% 1.4 84% 98% 48% 1.5 83-86% 99% 54% 1.6 86% 99% 57% 2.0 83% 93% 63% [0051] The only impurity present in the final solid reaction product was creatine HCl when 1.3 to 1.6 mole equivalents of acetyl chloride were employed. Creatinine HCl was the only impurity identified when 2.0 equivalents were employed. These results indicate that 1.5 to 1.6 equivalents of acetyl chloride may be optimal as these conditions produced the greatest conversion and yield of the desired product with a high degree of purity. Higher amounts of acetyl chloride, such as greater than 2.0 mole equivalents, are less desirable despite the higher yields because of the greater production of the undesired creatinine HCl reaction byproduct. [0052] D. Composition of Starting Ethanol [0053] The composition of the starting ethanol to which the acetyl chloride is added was varied between a 100:0 and 80:20 ratio (v/v) of ethanol (EtOH) to ethyl acetate (EtOAc). The results of these experiments are presented in Table 3. [TABLE-US-00003] TABLE 3 EtOH:EtOAc Product Product (v/v) Conversion Purity Yield 100:0 83-86% 99% 54% 95:5 88% 96% 65% 90:10 87% 93% 64% 80:20 84% 93% 64% [0054] These data indicate that the 95:5 EtOH:EtOAc ratio (v/v) may be preferred because the increase in yield likely outweighs the slight loss in purity. One notable disadvantage with using larger amounts of EtOAc is that the reaction impurities consisted of about a 3:1 molar ratio of creatinine HCl:creatine HCl. Filtering the reaction mixture at a slightly higher temperature would improve the purity of the isolated CEE HCl, but as noted hereinabove (see part B) such an increase in temperature may result in a concomitant decrease in yield. [0055] Notably, all of the acetyl chloride added to the ethanol is also converted to EtOAc. Therefore the actual ratio of EtOH:EtOAc at the time of creatine monohydrate addition is different than the starting material. [0056] A number of literature and patent references are cited in the foregoing application in order to more fully describe the state of the art to which this invention pertains. The entire disclosure of each of these citations is incorporated by reference herein. [0057] While certain embodiments of the present invention have been described and/or specifically exemplified above, various other embodiments will be apparent to those skilled in the art from the foregoing disclosure. The present invention is, therefore, not limited to such embodiments, but is capable of considerable variation and modification without departing from the scope of the following claims.

Reference： [1]Patent: US2005/49428,2005,A1 .Location in patent: Page/Page column 3
[2]Patent: US2005/49428,2005,A1 .Location in patent: Page/Page column 3-4

7
[ 60-27-5 ]
[ 64-17-5 ]
[ 15366-32-2 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 5173 - 5181

8
[ 128-44-9 ]
[ 15366-32-2 ]
amino((2-ethoxy-2-oxoethyl)(methyl)amino)methaniminium 3-oxo-3H-benzo[d]isothiazol-2-ide 1,1-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In ethanol; at 50℃; for 4h;	To the solution of CEE hydrochloride 22 (1 .0 mmol, 195 mg) in EtCH (15 mL)equimolar quantity of sweetener salt (potassium 6-methyl-4-oxo-4H-1 ,2,3-oxathiazin-3-ide2,2-dioxide 0.201 g for 20a and sodium benzo[d]isothiazol-3-olate 1,1-dioxide hydrate 0.205g for 20b) was added and the mixture was then stirred for 4h at the 50 C. Sodium or potassium chloride, formed during the reaction, was separated by filtration through the 22 micron membrane filter and the filtrate was taken to dryness. Diethyl ether was added to the products and after it was evaporated, products 23a and 23b were isolated as white solids in quantitative yields.

Reference： [1]Patent: WO2018/208647,2018,A1 .Location in patent: Page/Page column 23; 28; 29

9
[ 15366-32-2 ]
[ 145-42-6 ]
amino((2-ethoxy-2-oxoethyl)(methyl)amino)methaniminium 2-((R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamido)ethane-1-sulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In ethanol; at 50℃; for 4h;	To the solution of CEE hydrochloride 22(1.0 mmol, 0.195 g) in EtCH (15 mL) equimolar quantity of sodium taurocholate hydrate 24(1 .0 mmol, 0.538 g) was added and the mixture was then stirred for 4h at the 50 C. Sodium chloride, formed during the reaction, was separated by filtration through the 22 micron membrane filter and the filtrate was taken to dryness. Diethyl ether was added to the product and after evaporation, product 26 was isolated as white solid in quantitative yield.White solid (95%, 0.641 g, 0.95 mmol). M.p. 179.4-195.4 C; 1H NMR (500 MHz,CD3OD, 5)4.27-4.23 (m, 1H), 4.19 (5, 1H), 3.95 (5, 1H), 3.79 (5, 1H), 3.58 (t, J= 7.0 Hz,2H), 3.49 (q, J= 7.0 Hz, 1H), 3.40-3.35 (m, 2H), 3.19 (5, 2H), 3.07 (5, 1H), 2.96 (t, J= 3.0Hz, 2H), 2.31-2.23 (m, 3H), 2.14-2.07 (m, 1H), 2.02-1.92 (m, 2H), 1.90-1.83 (m, 2H), 1.82-1.71 (m, 3H), 1.67-1.61.4 (m, 1H), 1.61-1.51 (m, 5H), 1.43-1.26 (m, 6H), 1.17 (t, J= 7.1, 2H),1.12-1.09 (m, 1H), 1.03 (d, J= 6.1 Hz, 2H), 0.98-0.95 (m, 2H), 0.91 (5, 3H), 0.71 (brs, 3H).l3 NMR (125 MHz, CD3OD) O 177.0, 169.8, 160.0, 74.5, 73.3, 69.5, 63.4, 58.8, 53.1, 52.0,48.5, 48.0, 43.6, 43.5, 41.5, 40.9, 38.4, 37.4, 37.1, 36.4, 34.7, 33.6, 31.7, 30.1, 29.1, 28.3,24.7, 23.7, 18.9, 18.3, 14.9, 13.5. HRMS(ESI) calcd for C6H14N302 [M+H] 160.1081, found160.1080; HRMS (ESI) calcd for C26H44N075 [M-H]- 514.2844, found 514.2830.

Reference： [1]Patent: WO2018/208647,2018,A1 .Location in patent: Page/Page column 24; 25; 29; 30

10
[ 55589-62-3 ]
[ 15366-32-2 ]
amino((2-ethoxy-2-oxoethyl)(methyl)amino)methaniminium 6-methyl-4-oxo-4H-1,2,3-oxathiazin-3-ide 2,2-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	In ethanol; at 50℃; for 4h;	To the solution of CEE hydrochloride 22 (1 .0 mmol, 195 mg) in EtCH (15 mL)equimolar quantity of sweetener salt (potassium 6-methyl-4-oxo-4H-1 ,2,3-oxathiazin-3-ide2,2-dioxide 0.201 g for 20a and sodium benzo[d]isothiazol-3-olate 1,1-dioxide hydrate 0.205g for 20b) was added and the mixture was then stirred for 4h at the 50 C. Sodium or potassium chloride, formed during the reaction, was separated by filtration through the 22 micron membrane filter and the filtrate was taken to dryness. Diethyl ether was added to the products and after it was evaporated, products 23a and 23b were isolated as white solids in quantitative yields.White solid (97%, 0.312 g, 0.97 mmol). M.p. 118.9- 122.0 C; 1H NMR (500 MHz, CD3OD, 5)5.56(s, 1H), 4.30-4.24 (m, 4H), 3.11 (5, 3H), 2.09 (5, 3H), 1.33 (t, J= 7.2 Hz, 3H); 13C NMR (125 MHz, CD3OD, 5)173.2, 169.8, 164.4, 160.0, 102.7, 63.4, 53.1, 38.4,20.3, 14.9. HRMS (ESI) calcd for C6H14N302 [M+H] 160.1081, found 160.1079; HRMS (ESI) calcd for C4H4N045 [M-H]- 161 .9867, found 161 .9868.

Reference： [1]Patent: WO2018/208647,2018,A1 .Location in patent: Page/Page column 23; 28

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 15366-32-2 ]

Amino Acid

[ 57-00-1 ]

2-(1-Methylguanidino)acetic acid

Similarity: 0.80

[ 352-97-6 ]

2-Guanidinoacetic acid

Similarity: 0.70

Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
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Code	Phrase
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P222	Do not allow contact with air.
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P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P270	Do not eat, drink or smoke when using this product.
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P272	Contaminated work clothing should not be allowed out of the workplace.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P285	In case of inadequate ventilation wear respiratory protection.
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P235 + P410	Keep cool. Protect from sunlight.
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Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
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P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
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. 15366-32-2 ] {[proInfo.proName]}

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[ 15366-32-2 ] Synthesis Path-Upstream 1~4

[ 15366-32-2 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 15366-32-2 ]

Amino Acid

Precautionary Statements-General

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Health hazards

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[ 15366-32-2 ]