[ CAS No. 22204-53-1 ]

Name: 22204-53-1|(S)-2-(6-Methoxynaphthalen-2-yl)propanoic acid|98%
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SKU: A296148
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{[proInfo.proName]} (Synonyms:(S)-Naproxen) ,{[proInfo.pro_purity]}

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Quality Control of [ 22204-53-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 22204-53-1 ]

SDS Specification

Alternatived Products of [ 22204-53-1 ]

Product Details of [ 22204-53-1 ]

CAS No. :	22204-53-1	MDL No. :	MFCD00010500
Formula :	C₁₄H₁₄O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	230.26 g/mol	Pubchem ID :	-
Synonyms :	1. Naproxen

Calculated chemistry of [ 22204-53-1 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.21
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	66.79
TPSA :	46.53 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) :	-5.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.95
Log Po/w (XLOGP3) :	3.34
Log Po/w (WLOGP) :	3.04
Log Po/w (MLOGP) :	2.57
Log Po/w (SILICOS-IT) :	2.9
Consensus Log Po/w :	2.76

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.61
Solubility :	0.0566 mg/ml ; 0.000246 mol/l
Class :	Soluble
Log S (Ali) :	-3.99
Solubility :	0.0233 mg/ml ; 0.000101 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.02
Solubility :	0.0221 mg/ml ; 0.0000962 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.85

Safety of [ 22204-53-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P201-P202-P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P308+P313-P332+P313-P337+P313-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335-H361	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 22204-53-1 ]

* 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 [ 22204-53-1 ]
Downstream synthetic route of [ 22204-53-1 ]

[ 22204-53-1 ] Synthesis Path-Upstream 1~1

1
[ 22204-53-1 ]
[ 302-17-0 ]
[ 67-66-3 ]
[ 513-88-2 ]
[ 918-00-3 ]

Reference： [1] RSC Advances, 2017, vol. 7, # 53, p. 33627 - 33634

[ 22204-53-1 ] Synthesis Path-Downstream 1~59

1
[ 201230-82-2 ]
[ 63444-51-9 ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Reference： [1]Journal of the American Chemical Society,1990,vol. 112,p. 2803 - 2804
[2]Journal of the American Chemical Society,1990,vol. 112,p. 2803 - 2804

2
[ 30012-51-2 ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Yield	Reaction Conditions	Operation in experiment
	With Thermotoga maritima esterase Tm1160; In aq. acetate buffer; at 70℃;pH 5.5;Enzymatic reaction;	General procedure: Enzymatic reactions were carried out at 70 C in 1 ml of a reaction mixture containing the purified enzyme (0.235 mg) and 25 mg of racemic ketoprofen ethyl ester dissolved in 50 mM sodium acetate buffer (pH 5.5). The reaction mixture was stirred at 200 rpm. The resulting solution was analyzed by HPLC using the chiral column (25 cm × 4.6 cm, Daical Chemical Industries, Tokyo, Japan). Samples were eluted with n-hexane:2-propanol:acetic acid (90:10:0.5, v/v/v) at a flow rate of 1.0 mL/min and detected at 254 nm. The retention times of racemic ketoprofen ethyl ester, R-ketoprofen, and S-ketoprofen were detected at 5.4, 14.8 and 18.2 min, respectively. The enantioselectivity of the enzyme was calculated with E = ln[1 - c(1 + eep)]/ln[1 - c(1 - eep)], where c and eep represent the degree of conversion and the enantiomeric excess of product, respectively [34].

Reference： [1]Agricultural and Biological Chemistry,1981,vol. 45,p. 1389 - 1392
[2]Journal of Catalysis,2007,vol. 247,p. 194 - 200
[3]Journal of Molecular Catalysis B: Enzymatic,2013,vol. 85-86,p. 23 - 30

3
[ 27602-79-5 ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Yield	Reaction Conditions	Operation in experiment
	With C70H72IrO4P2(1+)*BF4(1-); hydrogen; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; under 3750.38 Torr; for 16h;Autoclave;	General procedure: The diastereomeric ratio of the used catalysts was determined by NMR prior to the catalysis. All catalysts and small amounts of liquids were added to the reaction mixture by means of stock solutions. All stock solutions were prepared using anhydrous, degassed solvents. In general, the hydrogenation reactions were carried out using anhydrous, degassed solvents. The catalyst solution, the substrate and, if applicable, the additive were solved in a Schlenk flask in the same solvent used for the stock solutions. A stainless steel autoclave loaded with a NMR tube and a small stirring bar was evacuated and flushed with argon three times before the reaction mixture was transferred into the NMR tube. As soon as the hydrogen gas line was purged with hydrogen gas at least seven times, the autoclave was pressurized with hydrogen gas. After the indicated period of time, the hydrogen gas was discharged from the autoclave. The conversion of the reaction was determined by NMR and the enantiomeric ratio of the product by enantioselective HPLC analysis.
	With C72H64IrO6P2(1+)*BF4(1-); hydrogen; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; under 3750.38 Torr; for 16h;Autoclave;	General procedure: The diastereomeric ratio of the used catalysts was determined by NMR prior to the catalysis. All catalysts and small amounts of liquids were added to the reaction mixture by means of stock solutions. All stock solutions were prepared using anhydrous, degassed solvents. In general, the hydrogenation reactions were carried out using anhydrous, degassed solvents. The catalyst solution, the substrate and, if applicable, the additive were solved in a Schlenk flask in the same solvent used for the stock solutions. A stainless steel autoclave loaded with a NMR tube and a small stirring bar was evacuated and flushed with argon three times before the reaction mixture was transferred into the NMR tube. As soon as the hydrogen gas line was purged with hydrogen gas at least seven times, the autoclave was pressurized with hydrogen gas. After the indicated period of time, the hydrogen gas was discharged from the autoclave. The conversion of the reaction was determined by NMR and the enantiomeric ratio of the product by enantioselective HPLC analysis.

Reference： [1]Tetrahedron Asymmetry,1994,vol. 5,p. 675 - 690
[2]Journal of Organic Chemistry,1994,vol. 59,p. 3064 - 3076
[3]Tetrahedron Asymmetry,1997,vol. 8,p. 177 - 179
[4]Journal of Organometallic Chemistry,1998,vol. 567,p. 163 - 171
[5]Journal of the American Chemical Society,1999,vol. 121,p. 7407 - 7408
[6]Journal of the American Chemical Society,1999,vol. 121,p. 7407 - 7408
[7]Journal of the American Chemical Society,1999,vol. 121,p. 7407 - 7408
[8]Journal of the American Chemical Society,2000,vol. 122,p. 11513 - 11514
[9]Tetrahedron Letters,2002,vol. 43,p. 2789 - 2792
[10]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1867 - 1871
[11]Synthetic Communications,2003,vol. 33,p. 175 - 182
[12]Journal of the American Chemical Society,2006,vol. 128,p. 5955 - 5965
[13]Advanced Synthesis and Catalysis,2006,vol. 348,p. 2172 - 2182
[14]Organic Letters,2002,vol. 4,p. 4599 - 4602
[15]European Journal of Organic Chemistry,2012,p. 6737 - 6744
[16]Synthesis,2017,vol. 49,p. 3485 - 3494
[17]Synthesis,2017,vol. 49,p. 3485 - 3494

4
(R)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester [ No CAS ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 6553 - 6556

5
[ 134435-65-7 ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1991,p. 485 - 486

6
[ 54656-96-1 ]
[ 52344-67-9 ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Reference： [1]Chemistry Letters,1984,p. 1431 - 1434

7
[ 27854-88-2 ]
[ 52344-67-9 ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Reference： [1]Chemistry Letters,1984,p. 1431 - 1434

8
[ 107951-72-4 ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Reference： [1]Chemistry Letters,1986,p. 1471 - 1472

9
[ 32305-59-2 ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Reference： [1]Journal of the American Chemical Society,1987,vol. 109,p. 7122 - 7127

10
[ 119408-04-7 ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Reference： [1]Gazzetta Chimica Italiana,1988,vol. 118,p. 451 - 456
[2]Gazzetta Chimica Italiana,1988,vol. 118,p. 451 - 456

11
[ 23981-80-8 ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium acetate;Resolution of racemate;Purification / work up;	Enantiomers of test racemates TR 19-23, of known drugs from the non-steroidal antiinflammatory group, were separated on analytical HPLC columns (250 mm x 4,6 mm), filled with CSP-4 or CSP-3. Since these compounds are structurally free carboxyl acids, it was necessary to use a polar mobile phase containing a certain amount of ammonium acetate. Results obtained by the enantioselective separation of these compounds are shown in Table 5 and the chromatogram achieved for the enantiomers of naproxen is shown in Figure 8. <n="20"/>TABLE 5 Enantiomer separations for test racemate TR 20-23 on the column filled withCSP-3 (250 mm x 4.6 mm ID), with hexane : 2-PrOH = 8:2 + lg/L NH4OAc as the mobile phase, 1 ml/min, 254 nm.

Reference： [1]Tetrahedron Asymmetry,2001,vol. 12,p. 3015 - 3018
[2]Analytical chemistry,1995,vol. 67,p. 2088 - 2095
[3]Patent: WO2009/109792,2009,A1 .Location in patent: Page/Page column 18; Figure 8
[4]Chirality,2010,vol. 22,p. 479 - 485
[5]Chemistry Letters,2011,vol. 40,p. 266 - 267
[6]RSC Advances,2016,vol. 6,p. 24835 - 24842
[7]Chemical Communications,2017,vol. 53,p. 1470 - 1473
[8]Chemical Communications,2017,vol. 53,p. 509 - 512
[9]Angewandte Chemie - International Edition,2019,vol. 58,p. 11479 - 11482
Angew. Chem.,2019,vol. 131,p. 11603 - 11606,4

12
(3S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl α-(6-methoxy-2-naphthyl)propionate [ No CAS ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Reference： [1]Tetrahedron Asymmetry,1995,vol. 6,p. 991 - 1000

13
2-(6-Methoxy-naphthalen-2-yl)-propionic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester [ No CAS ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Reference： [1]Journal of the American Chemical Society,1995,vol. 117,p. 12159 - 12171

14
[ 622-40-2 ]
2-(6-Methoxy-naphthalen-2-yl)-thiopropionic acid S-(2,2,2-trifluoro-ethyl) ester [ No CAS ]
[ 1544-53-2 ]
[ 22204-53-1 ]
[ 23979-41-1 ]
(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid 2-morpholin-4-yl-ethyl ester [ No CAS ]
(R)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid 2-morpholin-4-yl-ethyl ester [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 2799 - 2807

15
[ 26159-36-4 ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1998,vol. 37,p. 1221 - 1227

16
[ 2700-47-2 ]
[ 22204-53-1 ]

Reference： [1]Synthetic Communications,2002,vol. 32,p. 1697 - 1702
[2]Synthetic Communications,2001,vol. 31,p. 1047 - 1051

17
2-(6-methoxy-2-naphthyl)-2-methyl-t-butyldimethylsilylketene S-methyl thioacetal [ No CAS ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Reference： [1]Tetrahedron Asymmetry,2003,vol. 14,p. 119 - 125

18
[ 105052-64-0 ]
[ 22204-53-1 ]
[ 23979-41-1 ]
[ 124649-62-3 ]
(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid 2-chloro-ethyl ester [ No CAS ]