[ CAS No. 1008526-71-3 ] {[proInfo.proName]}

Name: 1008526-71-3|tert-Butyl 3-(aminomethyl)-3-hydroxyazetidine-1-carboxylate|95%
Brand: Ambeed
SKU: A411166
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Quality Control of [ 1008526-71-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1008526-71-3 ]

SDS Specification

Alternatived Products of [ 1008526-71-3 ]

Product Details of [ 1008526-71-3 ]

CAS No. :	1008526-71-3	MDL No. :	MFCD17015986
Formula :	C₉H₁₈N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NVEHYSKQUSAZBP-UHFFFAOYSA-N
M.W :	202.25	Pubchem ID :	57415900
Synonyms :

Calculated chemistry of [ 1008526-71-3 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.89
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	55.69
TPSA :	75.79 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) :	-8.14 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.11
Log Po/w (XLOGP3) :	-0.85
Log Po/w (WLOGP) :	-0.45
Log Po/w (MLOGP) :	-0.27
Log Po/w (SILICOS-IT) :	-0.34
Consensus Log Po/w :	0.04

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.29
Solubility :	103.0 mg/ml ; 0.508 mol/l
Class :	Very soluble
Log S (Ali) :	-0.26
Solubility :	111.0 mg/ml ; 0.549 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.41
Solubility :	78.5 mg/ml ; 0.388 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.33

Safety of [ 1008526-71-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1008526-71-3 ]

* 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 [ 1008526-71-3 ]

[ 1008526-71-3 ] Synthesis Path-Downstream 1~22

1
[ 1008526-70-2 ]
[ 1008526-71-3 ]

Yield	Reaction Conditions	Operation in experiment
68%	With hydrogen;palladium 10% on activated carbon; In ethanol; at 50.0℃; under 2585.81 Torr; for 2.0h;	INTERMEDIATE 343-(Aminomethyl)-3-hydroxyazetidine-l-carboxylic acid ferf-butyl ester; Intermediate 33 (500 mg, 2.2 mmol) was dissolved in ethanol (40 mL) in a hydrogenation vessel and 10% palladium on charcoal (43 mg) was added. The vessel was charged with hydrogen to 50 psi and heated to 500C. This was then stirred for 2 h and the catalyst was removed by filtering through a plug of celite. The solvent was removed under reduced pressure to yield a pale yellow oil. This was purified by chromatography on an amine column using DCM/MeOH 5% as the eluent to afford the title compound (306 mg, 68%). deltaH (d6-DMSO) 5.50 (IH, s), 3.73 (2H, d, J 8.5 Hz), 3.54 (2H, d, J 8.5 Hz), 2.60 (2H, s), 1.37 (9H, s). Some exchangeable protons were not observed.
68%	With hydrogen;palladium 10% on activated carbon; In ethanol; at 50.0℃; under 2585.81 Torr; for 2.0h;	INTERMEDIATE 113-(Ammomethyl)-3-hydroxyazetidine trifluoroacetate saltIntermediate 10 (500 mg, 2.2 mmol) was dissolved in ethanol (40 mL) in a hydrogenation vessel and 10% palladium on charcoal (43 mg) was added. The vessel was charged with hydrogen to 50 psi and heated to 5O0C. This was then stirred for 2 h and the catalyst was removed by filtering through a plug of celite. The solvent was removed under reduced pressure to yield a pale yellow oil. The intermediate was purified by chromatography on an amine column using 5% DCM/MeOH as the eluent to afford the BOC-protected amine as an off-white solid (306 mg, 68%). ?H (d6-DMSO) 5.50 (IH, s), 3.73 (2H, d, J8.5 Hz), 3.54 (2H, d, J8.5 Hz), 2.60 (2H, s), 1.37 (9H, s). Some exchangeable protons were not observed. The intermediate BOC-protected amine was dissolved in DCM (10 mL) and trifluoroacetic acid (1 mL) added. The mixture was stirred for 1 hour at room temperature before the volatiles were removed in vacuo to give the title compound, which was used without further purification.
	With palladium 10% on activated carbon; hydrogen; In methanol; at 20.0℃; under 775.743 Torr; for 16.0h;	3-Hydroxy-3-(nitromethyl)azetidin-1-carboxylic acid tert-butyl ester (6.00g, 25.84 mmol) was dissolved in methanol (60.00 mL) at 20 C, and added with wet palladium on carbon (10%, 0.6 g) under nitrogen protection. The suspension was degassed, displaced,and purified with hydrogen gas four times, and then stirred under hydrogen atmosphere (15 psi) at 20 C for 16 hours. TLC (petroleum ether: ethyl acetate=): 1) showed that the reaction was complete. The reaction mixture was filtered and concentrated under vacuum to give compound 13B. 1H NMR (400MHz, DMSO-d6) delta = 5.55 (br s, 1H), 3.87 (br d, J=7.9 Hz, 1H), 3.73 (br d, J=7.8 Hz, 1H), 3.63 - 3.51 (m, 2H), 2.90 (s, 1H), 2.59 (s, 1H), 1.36 (s, 9H).

13 g

With palladium 10% on activated carbon; hydrogen; In ethanol; at 1650.0℃;

To a solution oftert-butyl 3-hydroxy-3- (nitromethyl) azetidine-1-carboxylate (20g, 0.09 mol) in EtOH (200mL) was added Pd/C (2 g, 10%wt) and the reaction mixture was degassed under N 2 atmosphere for three times and stirred under H 2at 50 for 16 hrs. The mixture was filtered and the filtrate was concentrated to dryness. The residue was purified by silica gel chromatography (DCM: MeOH = 50: 1) to give desired product (13.0g, 75%yield) as colorless oil. MS (ESI) m/z: 103 (M+H-100) +.

Reference： [1]Patent: WO2008/20206,2008,A2 .Location in patent: Page/Page column 45
[2]Patent: WO2009/13462,2009,A1 .Location in patent: Page/Page column 29-30
[3]Patent: EP3567030,2019,A1 .Location in patent: Paragraph 0210; 0212
[4]Patent: WO2020/57511,2020,A1 .Location in patent: Page/Page column 145

2
[ 1008526-71-3 ]
[ 1008526-44-0 ]
3-([2-(2-fluoro-4-iodophenylamino)-5,5-dimethyl-8-oxo-5,6,7,8-tetrahydro-4H-thieno[2,3-c]azepin-3-ylcarbonyl]amino}methyl)-3-hydroxyazetidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With triethylamine; In N,N-dimethyl-formamide;	EXAMPLE 743-([2-(2-Fluoro-4-iodophenylamino)-5,5-dimethyl-8-oxo-5,6,7,8-tetrahydro-4H'- thieno f 2, 3 -c] azepin-3 -ylcarbonyl] amino } methyl)- 3 -hydroxyazetidine- 1 -carboxylic acid tert-hlambdaxyl ester; Intermediate 34 (100 mg, 0.50 mmol) was dissolved in DMF (4.5 mL) and Intermediate 5 (289 mg, 0.45 mmol) and triethylamine (70 muL) were added sequentially. The reaction mixture was stirred overnight and the DMF was removed under reduced pressure. The resulting solid was dissolved in DCM (25 mL) and extracted with aqNaHCO3 (25 mL), aq citric acid (25 mL) and brine (25 mL). The organic layer was dried with sodium sulfate and the solvent removed to yield a pale solid. This was purified using silica gel chromatography (DCM to DCM/MeOH 5%) to yield a white solid which was triturated with 50:50 MeCN/isopropyl ether and dried to yield the title compound (198 mg, 73%). deltaH (d6-DMSO) 9.06 (IH, s), 8.07-8.03 (IH, m), 7.95-7.90 (IH, m), 7.64 (IH, d, J 12.2 Hz), 7.52-7.48 (IH, m), 7.15 (IH, t, J9.0 Hz), 5.86 (IH, s), 3.82 (2H, d, J 9.0 Hz), 3.62-3.57 (2H, m), 3.41-3.37 (2H, m), 2.88 (2H, d, J4.8 Hz), 2.73 (2H, s), 1.35 (9H, s), 0.95 (6H, s). LCMS (ES+) RT (pH 10) 2.02 minutes, 659 (M+H)+.

Reference： [1]Patent: WO2008/20206,2008,A2 .Location in patent: Page/Page column 80

3
[ 1008526-71-3 ]
[ 76-05-1 ]
3-(aminomethyl)-3-hydroxyazetidine trifluoroacetate salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; at 20℃; for 1h;	INTERMEDIATE 113-(Ammomethyl)-3-hydroxyazetidine trifluoroacetate saltIntermediate 10 (500 mg, 2.2 mmol) was dissolved in ethanol (40 mL) in a hydrogenation vessel and 10% palladium on charcoal (43 mg) was added. The vessel was charged with hydrogen to 50 psi and heated to 5O0C. This was then stirred for 2 h and the catalyst was removed by filtering through a plug of celite. The solvent was removed under reduced pressure to yield a pale yellow oil. The intermediate was purified by chromatography on an amine column using 5% DCM/MeOH as the eluent to afford the BOC-protected amine as an off-white solid (306 mg, 68%). ?H (d6-DMSO) 5.50 (IH, s), 3.73 (2H, d, J8.5 Hz), 3.54 (2H, d, J8.5 Hz), 2.60 (2H, s), 1.37 (9H, s). Some exchangeable protons were not observed. The intermediate BOC-protected amine was dissolved in DCM (10 mL) and trifluoroacetic acid (1 mL) added. The mixture was stirred for 1 hour at room temperature before the volatiles were removed in vacuo to give the title compound, which was used without further purification.

Reference： [1]Patent: WO2009/13462,2009,A1 .Location in patent: Page/Page column 29-30

4
[ 1008526-71-3 ]
[ 1446358-48-0 ]
C₂₆H₂₇F₂N₇O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In 1,4-dioxane; at 90℃;	General procedure: General procedure B A solution of amino nucleophile (3 equiv.), triethylamine (10 equiv.), and Intermediate 1 (1 equiv.) was stirred in dioxane and water (2:1 ratio) at 90 C until complete consumption of starting material was observed by LC/MS. The solution was diluted withiN hydrochloric acid and dichloromethane. The layers were then separated and thelayer was extracted with dichloromethane. The organics were combined, dried over magnesium sulfate, filtered, and the solvent was removed in vacuo. Purification yielded theproduct The title compound was prepared following general procedure B, except tert-butyl 3-(aminomethyl)-3-hydroxyazetidine- 1 -carboxylate was the amine reactant, and the reaction was run as a solution in dioxane. Ethyl acetate was used as solvent during work up. The crude material was purified via silica gel chromatography (0-5% methanol in dichloromethane gradient) to deliver the desired compound, Compound 1-351 (144 mg, quantitative yield) as a white solid. 1H-NMR (400 MHz, CD3OD) oe 8.76 (d, 1 H), 8.11 (d, 1 H), 7.44 (s, 1 H), 7.30-7.25 (m, 1 H),7.12-7.01 (m, 2 H), 6.92 (d, 1 H), 6.81 (t, 1 H), 5.97 (s, 2 H), 4.09 (d, 2 H), 3.93 (br s, 2 H), 3.78 (d, 2 H), 1.40 (s, 9 H).

Reference： [1]Patent: WO2014/144100,2014,A2 .Location in patent: Paragraph 00274

5
[ 1008526-71-3 ]
[ 530-62-1 ]
6-oxo-5-oxa-2,7-diazaspiro[3.4]octane-2-carboxylic acid tert-butyl ester [ No CAS ]