[ CAS No. 1346674-10-9 ] {[proInfo.proName]}

Name: 1346674-10-9|1-tert-Butyl 3-ethyl azetidine-1,3-dicarboxylate|97%
Brand: Ambeed
SKU: A286427
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Quality Control of [ 1346674-10-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1346674-10-9 ]

SDS Specification

Alternatived Products of [ 1346674-10-9 ]

Product Details of [ 1346674-10-9 ]

CAS No. :	1346674-10-9	MDL No. :	MFCD08704361
Formula :	C₁₁H₁₉NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GFAKQSWJCMKEGE-UHFFFAOYSA-N
M.W :	229.27	Pubchem ID :	53485131
Synonyms :

Calculated chemistry of [ 1346674-10-9 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.82
Num. rotatable bonds :	6
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	62.68
TPSA :	55.84 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) :	-6.91 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.95
Log Po/w (XLOGP3) :	1.11
Log Po/w (WLOGP) :	1.04
Log Po/w (MLOGP) :	1.03
Log Po/w (SILICOS-IT) :	0.86
Consensus Log Po/w :	1.4

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.56
Solubility :	6.25 mg/ml ; 0.0272 mol/l
Class :	Very soluble
Log S (Ali) :	-1.88
Solubility :	3.05 mg/ml ; 0.0133 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.2
Solubility :	14.3 mg/ml ; 0.0625 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.36

Safety of [ 1346674-10-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1346674-10-9 ]

* 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.

Downstream synthetic route of [ 1346674-10-9 ]

[ 1346674-10-9 ] Synthesis Path-Downstream 1~12

1
[ 1346674-10-9 ]
[ 177947-96-5 ]

Yield	Reaction Conditions	Operation in experiment
	With diisobutylaluminium hydride In dichloromethane Inert atmosphere;

Reference： [1]Kazmierski, Wieslaw M.; Maynard, Andrew; Duan, Maosheng; Baskaran, Sam; Botyanszki, Janos; Crosby, Renae; Dickerson, Scott; Tallant, Matthew; Grimes, Rick; Hamatake, Robert; Leivers, Martin; Roberts, Christopher D.; Walker, Jill [Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 2058 - 2073]

2
[ 1346674-10-9 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / dichloromethane / Inert atmosphere 2: benzene / Reflux; Inert atmosphere

3
[ 1346674-10-9 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: diisobutylaluminium hydride / dichloromethane / Inert atmosphere 2: benzene / Reflux; Inert atmosphere 3: triethylamine / tetrahydrofuran / Inert atmosphere

4
[ 1346674-10-9 ]
[ 1272656-39-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: diisobutylaluminium hydride / dichloromethane / Inert atmosphere 2: benzene / Reflux; Inert atmosphere 3: triethylamine / tetrahydrofuran / Inert atmosphere 4: hydrogen / ethanol / Inert atmosphere

5
[ 1346674-10-9 ]
[ 1272656-42-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: diisobutylaluminium hydride / dichloromethane / Inert atmosphere 2: benzene / Reflux; Inert atmosphere 3: triethylamine / tetrahydrofuran / Inert atmosphere 4: hydrogen / ethanol / Inert atmosphere 5: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

6
[ 1346674-10-9 ]
[ 1272656-44-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: diisobutylaluminium hydride / dichloromethane / Inert atmosphere 2: benzene / Reflux; Inert atmosphere 3: triethylamine / tetrahydrofuran / Inert atmosphere 4: hydrogen / ethanol / Inert atmosphere 5: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 6: lithium hydroxide / water; tetrahydrofuran; methanol / 2 h / 20 °C

7
[ 405090-31-5 ]
[ 24424-99-5 ]
[ 1346674-10-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: azetidine-3-carboxylic acid ethyl ester hydrochloride With triethylamine In dichloromethane at 0℃; for 0.5h; Stage #2: di-<i>tert</i>-butyl dicarbonate In dichloromethane at 0℃; for 3h;	267 Example 267 - Preparation of Intermediate 61 Example 267 - Preparation of Intermediate 61 The synthesis of Intermediate 61 followed the procedure of General Procedure 7 following: Intermediate 60 Intermediate 61 To a cooled solution (0°C) of ethyl azetidine-3-carboxylate hydrochloride (70 g, 424 mmol) in dichloromethane (700 mL) was added triethylamine (119 mL, 848 mmol) dropwise over 30 min, followed by di-tert butyl dicarbonate (111 g, 509 mmol). After stirring at this temperature for 3 hours, the mixture was concentrated under reduced pressure. The mixture was diluted with water (20 mL) and extracted into dichloromethane (3 x 100 mL). The combined organic layers were washed with brine (2 x 10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to give 1-(tert-butyl) 3-ethyl azetidine-1,3-dicarboxylate (Intermediate 61, 40 g, yield: 42%) as an oily residue that was used without further purification into the next step. m/z 230.23 [M+H]+; TLC System: 10% Methanol- dichloromethane; Rf- 0.7.

Reference： [1]Current Patent Assignee: VERSEON CORP - WO2016/138532, 2016, A1 Location in patent: Paragraph 0506

8
[ 75-05-8 ]
[ 1346674-10-9 ]
[ 887594-13-0 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hexamethyldisilazane In tetrahydrofuran for 2h;	268 Example 268 - Preparation of Intermediate 62 Example 268 - Preparation of Intermediate 62 The synthesis of Intermediate 62 followed the procedure of General Procedure 2 following: Intermediate 61 Intermediate 62 To a cooled (0°C) solution of 1-(tert-butyl) 3-ethyl azetidine-1,3-dicarboxylate (Intermediate 61, 1 g, 4.36 mmol in THF (50 mL), dry acetonitrile (0.32 mL, 8.7 mmol) was added. After 10 min, LHDMS (1M in THF, 8.7 mL, 8.7 mmol) was added. After stirring at 0°C for 2 hours, the mixture was quenched with saturated citric acid solution until pH=5 and extracted into Ethyl acetate (3 x 50 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to give tert-butyl 3-(2-cyanoacetyl)azetidine-1-carboxylate (Intermediate 62, 1.2 g, yield: 99%) as an oily residue that was used without further purification into the next step. m/z 225.02 [M+H]+; TLC System: 10% Methanol- dichloromethane; Rf-0.5.

Reference： [1]Current Patent Assignee: VERSEON CORP - WO2016/138532, 2016, A1 Location in patent: Paragraph 0507

9
[ 91-63-4 ]
[ 1346674-10-9 ]
[ 2247266-42-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; trifluoroacetic acid; sodium persulfate / acetonitrile; water / 21 h / 20 - 25 °C / Sealed tube; Inert atmosphere; Irradiation 2: trifluoroacetic acid / dichloromethane / 18 h / 20 - 25 °C

Reference： [1]Bosset, Cyril; Beucher, Hélène; Bretel, Guillaume; Pasquier, Elisabeth; Queguiner, Laurence; Henry, Cyril; Vos, Ann; Edwards, James P.; Meerpoel, Lieven; Berthelot, Didier [Organic Letters, 2018, vol. 20, # 19, p. 6003 - 6006]

10
[ 91-63-4 ]
[ 1346674-10-9 ]
[ 2247266-25-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium persulfate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; trifluoroacetic acid In water; acetonitrile at 20 - 25℃; for 21h; Sealed tube; Inert atmosphere; Irradiation; diastereoselective reaction;

11
[ 1346674-10-9 ]
[ 2646684-45-7 ]

Yield	Reaction Conditions	Operation in experiment
2.53 g	Stage #1: 1-(tert-butyl) 3-ethyl azetidine-1,3-dicarboxylate With lithium hexamethyldisilazane In tetrahydrofuran; ethylbenzene at -78℃; for 0.25h; Inert atmosphere; Stage #2: With carbon tetrabromide In tetrahydrofuran; ethylbenzene at 20℃; for 20h;	52.1 Step 1.1-(tert-Butyl) 3-ethyl 3-bromoazetidine-1,3-dicarboxylate. A mixture of LHMDS (1.0 M in THF/ethyl benzene, 15.8 mL, 15.8 mmol) and dry THF (60 mL) under N2 was cooled to -78°C. A solution of ethyl 1-boc-azetidine-3-carboxylate (3.01 g, 13.1 mmol) in dry THF (30 mL) was added dropwise, and the mixture was stirred at -78 °C for 15 min. A solution of CBr4 (6.56 g, 19.8 mmol) in dry THF (30 mL) was added dropwise, and the mixture was warmed to rt and stirred for 20h. The reaction mixture was diluted with Et2O (350 mL), washed with saturated aqueous NaHCO3 (2×250 mL) and brine (250 mL), dried over Na2SO4, decanted and concentrated. The residue was purified by flash chromatography (EtOAc/Hexanes) to afford the title compound (2.53g) as an orange oil.1H NMR (500 MHz, CDCl3) δ ppm 4.64 (dd, 2H), 4.25-4.33 (m, 4H), 1.45 (s, 9H), 1.33 (t, 3H).

Reference： [1]Current Patent Assignee: UNIVERSITY OF UTAH - WO2021/102314, 2021, A1 Location in patent: Paragraph 00243

12
[ 75-03-6 ]
[ 1346674-10-9 ]
[ 2737287-30-6 ]

Yield	Reaction Conditions	Operation in experiment
677 mg	With potassium hexamethylsilazane In tetrahydrofuran; toluene at -78 - 20℃;	A4.34.1 A4.34.1 3-Ethyl-azetidine-1,3-dicarboxylic acid 1 -tert-butyl ester 3-ethyl ester To a solution of ethyl 1-Boc-azetidine-3-carboxylate (993 mg) and iodoethane (0.338 mL) in THF (10 mL) was added potassium bis(trimethylsilyl)amide (1.55 mL) as a solution in toluene (10 mL) at -78°C. The reaction was stirred overnight and allowed to slowly warm up to RT. The reaction was quenched by the addition of aqueous aq. sat. NH4CI (20 mL) and diluted with water (20 mL) and EA (20 mL). The phases were separated and the aqueous phase was extracted with EA (3x, 30 mL). The combined organic phases were washed with brine, dried over MgS04 and concentrated in vacuo. The product was obtained as 677mg yellow oil. LC-MS (A) tR = 0.88min; [M+H]+: 257.16

Reference： [1]Current Patent Assignee: IDORSIA PHARMACEUTICALS LTD - WO2021/219849, 2021, A1 Location in patent: Page/Page column 150

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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
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H290	May be corrosive to metals
Health hazards
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H301	Toxic if swallowed
H302	Harmful if swallowed
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H312	Harmful in contact with skin
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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
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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
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H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
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H351	Suspected of causing cancer
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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. 1346674-10-9 ] {[proInfo.proName]}

Quality Control of [ 1346674-10-9 ]

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[ 1346674-10-9 ] Synthesis Path-Downstream 1~12

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Amides

Esters

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Aliphatic Heterocycles

Azetidines

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[ 1346674-10-9 ]

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[ 1346674-10-9 ]