[ CAS No. 92398-47-5 ] {[proInfo.proName]}

Name: 92398-47-5|Methyl 1-aminocyclobutanecarboxylate hydrochloride|97%
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SKU: A119267
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Quality Control of [ 92398-47-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 92398-47-5 ]

SDS Specification

Alternatived Products of [ 92398-47-5 ]

Product Details of [ 92398-47-5 ]

CAS No. :	92398-47-5	MDL No. :	MFCD04115288
Formula :	C₆H₁₂ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LLCSDOKIBIMJNU-UHFFFAOYSA-N
M.W :	165.62	Pubchem ID :	42614147
Synonyms :

Calculated chemistry of [ 92398-47-5 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.83
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.84
TPSA :	52.32 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.81 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.71
Log Po/w (WLOGP) :	0.84
Log Po/w (MLOGP) :	0.35
Log Po/w (SILICOS-IT) :	0.48
Consensus Log Po/w :	0.48

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.18
Solubility :	10.9 mg/ml ; 0.0657 mol/l
Class :	Very soluble
Log S (Ali) :	-1.39
Solubility :	6.8 mg/ml ; 0.041 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.66
Solubility :	36.5 mg/ml ; 0.22 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.4

Safety of [ 92398-47-5 ]

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 [ 92398-47-5 ]

* 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 [ 92398-47-5 ]
Downstream synthetic route of [ 92398-47-5 ]

[ 92398-47-5 ] Synthesis Path-Upstream 1~7

1
[ 67-56-1 ]
[ 22264-50-2 ]
[ 92398-47-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 0 - 20℃; for 0.12 h;	To a stirred solution of 1-aminocyclobutane-l-carboxylic acid (2.7 g, 23.4 mmol) in MeOH (40 ml), was carefully added acetyl chloride (4.2 ml, 58.6 mmol) drop wise at 0 °C. The reaction mixture was then warmed to room temperature and stirred for about 12 hours. After completion of the reaction (monitored by TLC), the reaction mixture was concentrated under reduced pressure to give methyl 1-aminocyclobutane-l -carboxylate hydrochloride (3.02 g, yield: 100 percent) as a white solid.To a stirred solution of methyl 1-aminocyclobutane-l -carboxylate hydrochloride (3.02 g, 23.4 mmol) in THF (40 ml), were added N(Et)₃(9.6 ml, 69.6 mmol) and (Boc)₂0 (6.4 ml, 23.8 mmol) at 0 °C. The reaction mixture was then warmed to room temperature and stirred for about 12 hours. After completion of the reaction (monitored by TLC), saturated NH₄C1 solution was added, extracted with EtOAc (2 X 100 mL). The combined organic phases were washed with brine, dried over Na₂S0₄and concentrated under reduced pressure to give the crude product. Purification by flash chromatography with EtOAc-hexane (3: 7) as an eluent to afford the desired product (5.32 g, yield: 100percent) as an oil. 1H NMR (300 MHz, DMSO-d₆): δ 7.64 (s, 1H), 3.60 (s, 3H), 2.44-2.38 (m, 2H), 2.14-2.04 (m, 2H), 1.88-1.80 (m, 2H), 1.36 (s, 9H).
78%	Cooling with ice; Reflux	1-Aminocyclobutamic acid (250 mg, 2.17 mmol) was dissolved in 10 mL of anhydrous methanol, 0.3 mL of thionyl chloride was added dropwise to the ice bath,Remove the ice bath and heat the reflux overnight.Evaporated to dryness under reduced pressure to give 1-aminocyclopropylcarboxylic acid hydrochloride (280 mg) as a white solid in 78percent yield.
71%	at 0 - 20℃; for 20 h;	1-aminocyclobutanecarboxylic acid (100 mg) was dissolved in 10 ml of methanol, and the reaction solution was cooled to 0°C.At 0-5°C, HCl gas was introduced and stopped after 2 hours. The reaction solution was warmed to room temperature and reacted at room temperature for 18 hours. The mixture was concentrated under reduced pressure to give a yellow oil.Add 15 ml of ether to the concentrate and stir for 30 minutes.Filtered to give 10 mg (71percent yield) of the title compound as a white solid.

Reference： [1] Patent: WO2017/17630, 2017, A1, . Location in patent: Page/Page column 80-81
[2] Journal of the American Chemical Society, 1997, vol. 119, # 49, p. 11807 - 11816
[3] Patent: CN104230766, 2017, B, . Location in patent: Paragraph 0382; 0383; 0384
[4] Patent: CN104341351, 2018, B, . Location in patent: Paragraph 0356-0359
[5] Journal of Medicinal Chemistry, 1984, vol. 27, # 12, p. 1663 - 1668
[6] Patent: US2006/183694, 2006, A1, . Location in patent: Page/Page column 23-24
[7] Patent: US2007/10455, 2007, A1, . Location in patent: Page/Page column 24
[8] Patent: US2008/14173, 2008, A1, . Location in patent: Page/Page column 25
[9] Patent: WO2003/99274, 2003, A1, . Location in patent: Page 61
[10] Patent: WO2003/99316, 2003, A1, . Location in patent: Page 80
[11] Patent: US2004/77551, 2004, A1, . Location in patent: Page/Page column 130
[12] Patent: WO2005/46712, 2005, A1, . Location in patent: Page/Page column 67; 68
[13] Patent: WO2005/51410, 2005, A1, . Location in patent: Page/Page column 68
[14] Patent: US2005/143316, 2005, A1, . Location in patent: Page/Page column 29
[15] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 12, p. 3502 - 3506
[16] Patent: US2008/119461, 2008, A1, . Location in patent: Page/Page column 30

2
[ 67-56-1 ]
[ 92398-47-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With thionyl chloride In dichloromethane at 20℃; for 3 h;	1-aminocyclobutanecarboxylic acid hydrochloride (5.2 g, 34.5 mmol) and methanol (120 ml) were charged. An ice bath was set, and thionyl chloride (3.7 ml, 51.7 mmol) was slowly added thereto. Then, the ice bath was removed, and the mixture was stirred at room temperature for 3 hours. The resultant product was vacuum-distilled to remove a solvent, and dried in a 60 oven so as to obtain methyl-1-aminocyclobutanecarboxylate hydrochloride (5.62 g, 37.1 mmol, 98 percent).[677] ¹H NMR (400 MHz, DMSO-d₆) δ 8.94 (br, 3H), 3.79 (s, 3H), 2.47 (m, 4H), 2.07 (m, 2H).
98%	at 20℃; for 3 h; Cooling with ice	Example 6 Preparation Example 1 Synthesis of N-4-(1-(2-nitrophenylsulfonamido)cyclobutanecarboxyamido)adamantane-1-carboxyami de (compound 145) 1-aminocyclobutanecarboxylic acid hydrochloride (5.2 g, 34.5 mmol) and methanol (120 ml) were charged. An ice bath was set and thionyl chloride (3.7 ml, 51.7 mmol) was slowly added thereto. Then, the ice bath was removed, and the mixture was stirred at room temperature for 3 hours. The resultant product was vacuum-distilled to remove a solvent, and dried in a 60° C. oven so as to obtain methyl-1-aminocyclobutanecarboxylate hydrochloride (5.62 g, 37.1 mmol, 98percent). ¹H NMR (400 MHz, DMSO-d₆) δ 8.94 (br, 3H), 3.79 (s, 3H), 2.47 (m, 4H), 2.07 (m, 2H).

Reference： [1] Patent: WO2013/19091, 2013, A2, . Location in patent: Paragraph 674-677
[2] Patent: US2014/206875, 2014, A1, . Location in patent: Paragraph 0371-0373; 0394-0396

3
[ 22264-50-2 ]
[ 92398-47-5 ]

Reference： [1] Patent: US2004/48802, 2004, A1,
[2] Patent: US2009/274648, 2009, A1,
[3] Patent: US2009/304626, 2009, A1,

4
[ 89691-88-3 ]
[ 92398-47-5 ]

Reference： [1] Journal of the American Chemical Society, 1997, vol. 119, # 49, p. 11807 - 11816

5
[ 28246-87-9 ]
[ 92398-47-5 ]

Reference： [1] Synthesis (Germany), 2015, vol. 47, # 17, p. 2523 - 2528

6
[ 56447-13-3 ]
[ 92398-47-5 ]

Reference： [1] Synthesis (Germany), 2015, vol. 47, # 17, p. 2523 - 2528

7
[ 24424-99-5 ]
[ 92398-47-5 ]
[ 880166-10-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine In tetrahydrofuran at 0 - 20℃; for 0.12 h;	To a stirred solution of 1-aminocyclobutane-l-carboxylic acid (2.7 g, 23.4 mmol) in MeOH (40 ml), was carefully added acetyl chloride (4.2 ml, 58.6 mmol) drop wise at 0 °C. The reaction mixture was then warmed to room temperature and stirred for about 12 hours. After completion of the reaction (monitored by TLC), the reaction mixture was concentrated under reduced pressure to give methyl 1-aminocyclobutane-l -carboxylate hydrochloride (3.02 g, yield: 100 percent) as a white solid.To a stirred solution of methyl 1-aminocyclobutane-l -carboxylate hydrochloride (3.02 g, 23.4 mmol) in THF (40 ml), were added N(Et)₃(9.6 ml, 69.6 mmol) and (Boc)₂0 (6.4 ml, 23.8 mmol) at 0 °C. The reaction mixture was then warmed to room temperature and stirred for about 12 hours. After completion of the reaction (monitored by TLC), saturated NH₄C1 solution was added, extracted with EtOAc (2 X 100 mL). The combined organic phases were washed with brine, dried over Na₂S0₄and concentrated under reduced pressure to give the crude product. Purification by flash chromatography with EtOAc-hexane (3: 7) as an eluent to afford the desired product (5.32 g, yield: 100percent) as an oil. 1H NMR (300 MHz, DMSO-d₆): δ 7.64 (s, 1H), 3.60 (s, 3H), 2.44-2.38 (m, 2H), 2.14-2.04 (m, 2H), 1.88-1.80 (m, 2H), 1.36 (s, 9H).

Reference： [1] Patent: WO2017/17630, 2017, A1, . Location in patent: Page/Page column 80-81

[ 92398-47-5 ] Synthesis Path-Downstream 1~88

1
[ 67-56-1 ]
[ 22264-50-2 ]
[ 92398-47-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With acetyl chloride; at 0 - 20℃; for 0.12h;	To a stirred solution of 1-aminocyclobutane-l-carboxylic acid (2.7 g, 23.4 mmol) in MeOH (40 ml), was carefully added acetyl chloride (4.2 ml, 58.6 mmol) drop wise at 0 C. The reaction mixture was then warmed to room temperature and stirred for about 12 hours. After completion of the reaction (monitored by TLC), the reaction mixture was concentrated under reduced pressure to give methyl 1-aminocyclobutane-l -carboxylate hydrochloride (3.02 g, yield: 100 %) as a white solid.To a stirred solution of methyl 1-aminocyclobutane-l -carboxylate hydrochloride (3.02 g, 23.4 mmol) in THF (40 ml), were added N(Et)3(9.6 ml, 69.6 mmol) and (Boc)20 (6.4 ml, 23.8 mmol) at 0 C. The reaction mixture was then warmed to room temperature and stirred for about 12 hours. After completion of the reaction (monitored by TLC), saturated NH4C1 solution was added, extracted with EtOAc (2 X 100 mL). The combined organic phases were washed with brine, dried over Na2S04and concentrated under reduced pressure to give the crude product. Purification by flash chromatography with EtOAc-hexane (3: 7) as an eluent to afford the desired product (5.32 g, yield: 100%) as an oil. 1H NMR (300 MHz, DMSO-d6): delta 7.64 (s, 1H), 3.60 (s, 3H), 2.44-2.38 (m, 2H), 2.14-2.04 (m, 2H), 1.88-1.80 (m, 2H), 1.36 (s, 9H).
78%	With thionyl chloride;Cooling with ice; Reflux;	1-Aminocyclobutamic acid (250 mg, 2.17 mmol) was dissolved in 10 mL of anhydrous methanol, 0.3 mL of thionyl chloride was added dropwise to the ice bath,Remove the ice bath and heat the reflux overnight.Evaporated to dryness under reduced pressure to give 1-aminocyclopropylcarboxylic acid hydrochloride (280 mg) as a white solid in 78% yield.
71%	With hydrogenchloride; at 0 - 20℃; for 20.0h;	1-aminocyclobutanecarboxylic acid (100 mg) was dissolved in 10 ml of methanol, and the reaction solution was cooled to 0C.At 0-5C, HCl gas was introduced and stopped after 2 hours. The reaction solution was warmed to room temperature and reacted at room temperature for 18 hours. The mixture was concentrated under reduced pressure to give a yellow oil.Add 15 ml of ether to the concentrate and stir for 30 minutes.Filtered to give 10 mg (71% yield) of the title compound as a white solid.

	With hydrogenchloride; for 20.0h;	6. Preparation of 1-aminocyclobutanecarboxylic acid methyl ester-hydrochloride 1-Aminocyclobutanecarboxylic acid (100 mg, 0.869 mmol) (Tocris) was dissolved in 10 mL of methanol. HCl gas was bubbled in for 2 hours. The reaction mixture was stirred for 18 hours, and then concentrated in vacuo to give 144 mg of a yellow oil. Trituration with 10 mL of diethyl ether provided 100 mg of the titled product as a white solid. 1H NMR (CDCl3) delta 2.10-2.25 (m, 1H), 2.28-2.42 (m, 1H), 2.64-2.82 (m, 4H), 3.87 (s, 3H), 9.21 (br s, 3H).
	With hydrogenchloride; for 20.0h;	Example 4 1-tert-butoxycarbonylamino-cyclopropane-carboxylic acid, shown below, is commercially available 1-aminocyclobutanecarboxylic acid methyl ester-hydrochloride was prepared. 1-Aminocyclobutanecarboxylic acid (100 mg, 0.869 mmol)(Tocris) was dissolved in 10 mL of methanol, HCl gas was bubbled in for 2 hours. The reaction mixture was stirred for 18 hours, and then concentrated in vacuo to give 144 mg of a yellow oil. Trituration with 10 mL of ether provided 100 mg of the desired product as a white solid. 1H NMR (CDCl3) delta 2.10-2.25 (m, 1H), 2.28-2.42 (m, 1H), 2.64-2.82 (m, 4H), 3.87 (s, 3H), 9.21 (br s, 3H).
	With hydrogenchloride; In diethyl ether; for 20.0h;	1-Aminocyclobutanecarboxylic acid (100 mg, 0.869 mmol) (Tocris) was dissolved in 10 mL of methanol. HCl gas was bubbled in for 2 hours. The reaction mixture was stirred for 18 hours, and then concentrated in vacuo to give 144 mg of a yellow oil. Trituration with 10 mL of diethyl ether provided 100 mg of the desired product as a white solid. 1H NMR (CDCl3) delta 2.10-2.25 (m, 1H), 2.28-2.42 (m, 1H), 2.64-2.82 (m, 4H), 3.87 (s, 3H), 9.21 (br s, 3H).
	With hydrogenchloride; for 20.0h;	1-aminocyclobutanecarboxylic acid (100 mg, 0.869 mmol) (Tocris) was dissolved in 10 mLof MeOH, HCI gas was bubbled in for 2h. The reaction mixture was stirred for 18 h, and then concentrated in vacuo to give 144 mg of a yellow oil. Trituration with 10 mL of ether provided 100 mg of the titled product as a whitesolid.'H NMR(CDCl3) No. 2.10-2. 25(m, 1H), 2.28-2. 42(m,1H), 2.64-2. 82 (m, 4H), 3.87 (s, 3H), 9.21 (br s, 3H).
	With hydrogenchloride; for 20.0h;	1-AMINOCYCLOBUTANECARBOXYLIC acid (100 mg, 0.869 mmol) (Tocris) was dissolved in 10 mL of MEOH, HC . gas was bubbled in for 2h. The reaction mixture was stirred for 18 h, and then concentrated in vacuo to give 144 mg of a yellow oil. Trituration with 10 mL of ether provided 100 mg of the titled product as a white SOLID. H NMR (CDC13) 8 2.10-2. 25 (m, 1H), 2.28-2. 42 (m, 1H), 2.64- 2.82 (m, 4H), 3.87 (s, 3H), 9.21 (br s, 3H).
	With hydrogenchloride; for 20.0h;	2. Preparation of 1-aminocyclobutanecarboxylic Acid Methyl Ester-Hydrochloride 1-aminocyclobutanecarboxylic acid (100 mg, 0.869 mmol)(Tocris) was dissolved in 10 mL of MeOH, HCl gas was bubbled in for 2h. The reaction mixture was stirred for 18 h, and then concentrated in vacuo to give 144 mg of a yellow oil. Trituration with 10 mL of ether provided 100 mg of the titled product as a white solid. 1H NMR (CDCl3) delta 2.10-2.25 (m, 1 H), 2.28-2.42 (m, 1 H), 2.64-2.82 (m, 4H), 3.87 (s, 3H), 9.21 (br s, 3H).
	With hydrogenchloride; for 20.0h;	IV. Preparation of 1-aminocyclobutanecarboxylic acid methyl ester hydrochloride 1-aminocyclobutanecarboxylic acid (100 mg, 0. 869 mol) (Tocris) was dissolved in 10 mL of MeOH, HC1 gas was bubbled in for 2h. The reaction mixture was stirred for 18 h, and then concentrated in vacuo to give 144 mg of a yellow oil. Trituration with 10 mL of ether provided 100 mg of the titled product as a white solid. 1H NMR (CDC13) 8 2.10-2. 25 (m, 1H), 2.28-2. 42 (m, 1H), 2.64-2. 82 (m, 4H), 3. 87 (s, 3H), 9.21 (br s, 3H).
	With hydrogenchloride; for 20.0h;	1-aminocyclobutanecarboxylic acid (100 mg, 0.869 mmol) (Tocris) was dissolved in 10 mL of MeOH, HC1 gas was bubbled in for 2h. The reaction mixture was stirred for 18 h, and then concentrated in vacuo to give 144 mg of a yellow oil. Trituration with 10 mL of ether provided 100 mg of the titled product as a white solid. 1H NMR (CDC13) 8 2.10-2. 25 (m, 1H), 2.28-2. 42 (m, 1H), 2.64-2. 82 (m, 4H), 3.87 (s, 3H), 9.21 (br s, 3H).
	With hydrogenchloride; for 20.0h;	1-aminocyclobutanecarboxylic acid (100 mg, 0.869 mmol) (Tocris) was dissolved in 10 mL of MeOH, HCl gas was bubbled in for 2 h. The reaction mixture was stirred for 18 h, and then concentrated in vacuo to give 144 mg of a yellow oil. Trituration with 10 mL of ether provided 100 mg of the titled product as a white solid. 1H NMR (CDCl3) delta 2.10-2.25 (m, 1H), 2.28-2.42 (m, 1H), 2.64-2.82 (m, 4H), 3.87 (s, 3H), 9.21 (br s, 3H)
	With hydrogenchloride; for 20.0h;	6. Preparation of 1-aminocyclobutanecarboxylic Acid Methyl ester-hydrochloride 1-Aminocyclobutanecarboxylic acid (100 mg, 0.869 mmol)(Tocris) was dissolved in 10 mL of methanol. HCl gas was bubbled in for 2 hours. The reaction mixture was stirred for 18 hours, and then concentrated in vacuo to give 144 mg of a yellow oil. Trituration with 10 mL of diethyl ether provided 100 mg of the desired product as a white solid. 1H NMR (CDCl3) delta 2.10-2.25 (m, 1H), 2.28-2.42 (m, 1H), 2.64-2.82 (m, 4H), 3.87 (s, 3H), 9.21 (br s, 3H).

Reference： [1]Patent: WO2017/17630,2017,A1 .Location in patent: Page/Page column 80-81
[2]Journal of the American Chemical Society,1997,vol. 119,p. 11807 - 11816
[3]Patent: CN104230766,2017,B .Location in patent: Paragraph 0382; 0383; 0384
[4]Patent: CN104341351,2018,B .Location in patent: Paragraph 0356-0359
[5]Journal of Medicinal Chemistry,1984,vol. 27,p. 1663 - 1668
[6]Patent: US2006/183694,2006,A1 .Location in patent: Page/Page column 23-24
[7]Patent: US2007/10455,2007,A1 .Location in patent: Page/Page column 24
[8]Patent: US2008/14173,2008,A1 .Location in patent: Page/Page column 25
[9]Patent: WO2003/99274,2003,A1 .Location in patent: Page 61
[10]Patent: WO2003/99316,2003,A1 .Location in patent: Page 80
[11]Patent: US2004/77551,2004,A1 .Location in patent: Page/Page column 130
[12]Patent: WO2005/46712,2005,A1 .Location in patent: Page/Page column 67; 68
[13]Patent: WO2005/51410,2005,A1 .Location in patent: Page/Page column 68
[14]Patent: US2005/143316,2005,A1 .Location in patent: Page/Page column 29
[15]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3502 - 3506
[16]Patent: US2008/119461,2008,A1 .Location in patent: Page/Page column 30

2
[ 1145-80-8 ]
[ 92398-47-5 ]
1-(2-Benzyloxycarbonylamino-3-hydroxy-propionylamino)-cyclobutanecarboxylic acid methyl ester [ No CAS ]