[ CAS No. 863304-76-1 ] {[proInfo.proName]}

Name: 863304-76-1|4-((tert-Butoxycarbonyl)amino)bicyclo[2.2.2]octane-1-carboxylic acid|97%
Brand: Ambeed
SKU: A144489
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Quality Control of [ 863304-76-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 863304-76-1 ]

SDS Specification

Alternatived Products of [ 863304-76-1 ]

Product Details of [ 863304-76-1 ]

CAS No. :	863304-76-1	MDL No. :	MFCD09835292
Formula :	C₁₄H₂₃NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PIRWVWMHESZXMT-UHFFFAOYSA-N
M.W :	269.34	Pubchem ID :	23150738
Synonyms :

Calculated chemistry of [ 863304-76-1 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.86
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	71.25
TPSA :	75.63 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.29
Log Po/w (XLOGP3) :	1.86
Log Po/w (WLOGP) :	2.69
Log Po/w (MLOGP) :	1.85
Log Po/w (SILICOS-IT) :	1.75
Consensus Log Po/w :	2.09

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.35
Solubility :	1.2 mg/ml ; 0.00445 mol/l
Class :	Soluble
Log S (Ali) :	-3.07
Solubility :	0.229 mg/ml ; 0.000852 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.4
Solubility :	1.07 mg/ml ; 0.00397 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.87

Safety of [ 863304-76-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 863304-76-1 ]

* 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 [ 863304-76-1 ]
Downstream synthetic route of [ 863304-76-1 ]

[ 863304-76-1 ] Synthesis Path-Upstream 1~2

1
[ 18720-35-9 ]
[ 863304-76-1 ]

Reference： [1] Patent: CN105732602, 2016, A,

2
[ 24424-99-5 ]
[ 863304-76-1 ]

Reference： [1] Patent: CN105732602, 2016, A,

[ 863304-76-1 ] Synthesis Path-Downstream 1~33

1
[ 863304-76-1 ]
[ 1201186-57-3 ]
tert-butyl 4-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)bicyclo[2.2.2]octan-1-ylcarbamate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4399 - 4404

2
[ 18720-35-9 ]
[ 863304-76-1 ]

Reference： [1]Patent: CN105732602,2016,A

3
[ 24424-99-5 ]
[ 863304-76-1 ]

Reference： [1]Patent: CN105732602,2016,A

4
methyl 4-(tert-butoxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylate [ No CAS ]
[ 863304-76-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With methanol; lithium hydroxide;	Compound BB-13-2 (0.056g, 0.2mmol) was dissolved in methanol (2.0mL), followed by addition of lithium hydroxide (2N,2mL), the reaction was treated with 1N hydrochloric pH4 ~ 5, and extracted with ethyl acetate (20mLx3) , washed with water, dried over sodium sulfate, spin dried to yield the titlecompound were BB-13-3 (white solid, 0.040 g, yield: 80%).

Reference： [1]Patent: CN105732602,2016,A .Location in patent: Paragraph 0259; 0261; 0262; 0265; 0266

5
[ 863304-76-1 ]
C₁₄H₂₅N₃O₃ [ No CAS ]

Reference： [1]Patent: CN105732602,2016,A

6
[ 863304-76-1 ]
C₁₅H₂₃N₃O₃ [ No CAS ]

Reference： [1]Patent: CN105732602,2016,A

7
[ 863304-76-1 ]
C₁₀H₁₅N₃O [ No CAS ]

Reference： [1]Patent: CN105732602,2016,A

8
[ 863304-76-1 ]
C₁₆H₂₅N₃O₃ [ No CAS ]

Reference： [1]Patent: CN105732602,2016,A

9
[ 863304-76-1 ]
C₁₁H₁₇N₃O [ No CAS ]

Reference： [1]Patent: CN105732602,2016,A

10
[ 863304-76-1 ]
C₂₄H₂₆F₃N₃O₃ [ No CAS ]

Reference： [1]Patent: CN105732602,2016,A

11
[ 863304-76-1 ]
[ 1068-57-1 ]
C₁₆H₂₇N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 3h;	Compound BB-13-3 (1.65g, 6.13mmol) was dissolved in N, N - dimethylformamide (20 mL), followed by addition ofacetyl hydrazide (0.499g, 6.74mmol), N, N - diisopropylethylamine amine (2.37g, 18.38mmol), 2- ( 7-benzotriazole azo-yl) - N, N, N ', N' - tetramethyluronium hexafluorophosphate (3.03g, 7.96mmol), the reaction It was stirred at room temperature for 3 hours.After completion of the reaction was added water, extracted with ethyl acetate (50 ml x), the organic phase was washed with brine (20 mL), dried over anhydrous sodiumsulfate, filtered, and concentrated to give the crude product.Fast by column (eluent, ethyl acetate / petroleum ether = 4/1) to give the title compound bb-14-1 (white solid, 1.6 g of, yield: 80%).

Reference： [1]Patent: CN105732602,2016,A .Location in patent: Paragraph 0275; 0277; 0278; 0279; 0280

12
[ 863304-76-1 ]
[ 5331-43-1 ]
C₂₂H₃₁N₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 26℃; for 16h;	The reaction was BB-13-3 (2.00g, 7.43mmol) was dissolved in N, N - dimethylformamide (20 mL), followed by additioncarbazate benzyl ester (1.23g, 7.43mmol), N, N - bis diisopropylethylamine (2.88g, 22.3mmol), 2- ( 7-azo-benzotriazole) - N, N, N ', N' - tetramethyluronium hexafluorophosphate (4.24g, 11.1 mmol).The reaction was stirred at 26 16hours.Was added water (40 mL), filtered, and the filter cake was dissolved in dichloromethane (50 mL), dried, filtered, and concentrated to give the title compound bb-13-4 (white solid, 2.5 g of, yield: 81%).

Reference： [1]Patent: CN105732602,2016,A .Location in patent: Paragraph 0259; 0261; 0262; 0267; 0268

13
[ 863304-76-1 ]
tert-butyl (4-(hydroxymethyl)bicyclo[2.2.2]octan-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With borane-THF; In tetrahydrofuran; at 0 - 20℃; for 3h;	B oranetetrahydrofuran complex (22.3 mL, 22.3 mmol, 1M) was added drop-wise to a solution at 0 C of <strong>[863304-76-1]4-((tert-butoxycarbonyl)amino)bicyclo[2.2.2]octane-1-carboxylic acid</strong> (3.0 g, 11 mmol) and anhydrous THF (5 mL). The resulting mixture was stirred at room temperature for 3 hours beforeslowly quenching with H20 (10 mL) and extracting with ethyl acetate (50 mL x 3). The combined organic extracts were washed with brine (35 mL), dried over anhydrous Mg504, filtered, concentrated to dryness under reduced pressure, and purified by flash column chromatography (eluent: petroleum ether: ethyl acetate = 1:1) to afford the title compound (2.8 g, 98%) as a colorless, sticky oil. ?H NIVIR (400 IVIFIz, DMSO-d6) oe 6.27 (br s, 1H), 4.28 (t, J 5.2Hz, 1H), 2.97 (d, J= 5.2 Hz, 1H), 1.74 - 1.59 (m, 6H), 1.42 - 1.25 (m, 15H)
	With BH3-DMS; In tetrahydrofuran; at 0 - 20℃;	To a solution of 4-((tert-butoxycarbonyl)amino)bicyclo[2.2.2]octane-1 -carboxylic acid (4.565g, 16.9minol) in THE (30mL) was added BH3-DMS (5.l5mL, 3.Oeq) at 0C. After addition, the reaction was further stirred overnight at rt. LC/MS indicated that the reaction was complete.The reaction was then treated with dropwise addition of 10% citric acid. Aqueous work up followed by ISCO purification (hexane/EtOAc) afforded tert-butyl (4- (hydroxymethyl)bicyclo[2.2.2]octan-1-yl)carbamate as a white solid. 1H NMR (400 MHz, DMSOd6) O 6.31 (s, 1H), 4.31 (t, J = 5.4 Hz, 1H), 2.99 (d, J = 5.4 Hz, 2H), 1.75- 1.61 (m, 6H), 1.41 - 1.27 (m, 15H). ESIMS (M÷H) 256.20.

Reference： [1]Patent: WO2018/112382,2018,A1 .Location in patent: Page/Page column 119
[2]Patent: WO2018/47081,2018,A1 .Location in patent: Page/Page column 63

14
[ 863304-76-1 ]
4-((tert-butoxycarbonyl)amino)bicyclo[2.2.2]octan-1-ylmethyl 4-(trifluoromethyl)benzenesulfonate [ No CAS ]