[ CAS No. 68208-19-5 ] {[proInfo.proName]}

Name: 68208-19-5|3-Amino-3-(3-methoxyphenyl)propanoic acid|95%
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SKU: A175935
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Quality Control of [ 68208-19-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 68208-19-5 ]

SDS Specification

Alternatived Products of [ 68208-19-5 ]

Product Details of [ 68208-19-5 ]

CAS No. :	68208-19-5	MDL No. :	MFCD00462569
Formula :	C₁₀H₁₃NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FGMPGCPZEOXEES-UHFFFAOYSA-N
M.W :	195.22	Pubchem ID :	2764294
Synonyms :

Calculated chemistry of [ 68208-19-5 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	51.99
TPSA :	72.55 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) :	-8.91 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.42
Log Po/w (XLOGP3) :	-2.0
Log Po/w (WLOGP) :	0.85
Log Po/w (MLOGP) :	0.82
Log Po/w (SILICOS-IT) :	0.9
Consensus Log Po/w :	0.4

Druglikeness

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

Water Solubility

Log S (ESOL) :	0.16
Solubility :	280.0 mg/ml ; 1.43 mol/l
Class :	Highly soluble
Log S (Ali) :	1.0
Solubility :	1960.0 mg/ml ; 10.0 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-2.0
Solubility :	1.97 mg/ml ; 0.0101 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.86

Safety of [ 68208-19-5 ]

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 [ 68208-19-5 ]

* 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 [ 68208-19-5 ]
Downstream synthetic route of [ 68208-19-5 ]

[ 68208-19-5 ] Synthesis Path-Upstream 1~6

1
[ 591-31-1 ]
[ 68208-19-5 ]

Reference： [1] Patent: US6291503, 2001, B1,

2
[ 141-82-2 ]
[ 591-31-1 ]
[ 68208-19-5 ]

Reference： [1] Tetrahedron Letters, 1991, vol. 32, # 44, p. 6327 - 6328
[2] Tetrahedron Letters, 1991, vol. 32, # 44, p. 6327 - 6328
[3] Journal of Medicinal Chemistry, 1996, vol. 39, # 17, p. 3238 - 3240
[4] European Journal of Organic Chemistry, 2013, # 3, p. 557 - 565

3
[ 100-83-4 ]
[ 68208-19-5 ]

Reference： [1] Archiv der Pharmazie (Weinheim, Germany), 1928, p. 119

4
[ 6099-04-3 ]
[ 68208-19-5 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1912, vol. 389, p. 36,111

5
[ 15854-56-5 ]
[ 68208-19-5 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1912, vol. 389, p. 36,111

6
[ 141-82-2 ]
[ 591-31-1 ]
[ 6099-04-3 ]
[ 68208-19-5 ]

Reference： [1] Archiv der Pharmazie (Weinheim, Germany), 1928, p. 119

[ 68208-19-5 ] Synthesis Path-Downstream 1~28

1
[ 6099-04-3 ]
[ 68208-19-5 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1912,vol. 389,p. 36,111

2
[ 15854-56-5 ]
[ 68208-19-5 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1912,vol. 389,p. 36,111

3
[ 141-82-2 ]
[ 591-31-1 ]
[ 6099-04-3 ]
[ 68208-19-5 ]

Reference： [1]Archiv der Pharmazie,1928,p. 119

4
[ 141-82-2 ]
[ 591-31-1 ]
[ 68208-19-5 ]

Reference： [1]Tetrahedron Letters,1991,vol. 32,p. 6327 - 6328
[2]Tetrahedron Letters,1991,vol. 32,p. 6327 - 6328
[3]Journal of Medicinal Chemistry,1996,vol. 39,p. 3238 - 3240
[4]European Journal of Organic Chemistry,2013,p. 557 - 565

5
[ 68208-19-5 ]
[ 76-05-1 ]
[ 138621-65-5 ]

Reference： [1]Bulletin de la Societe Chimique de France,1993,vol. 130,p. 121 - 124

6
[ 68208-19-5 ]
[ 407-25-0 ]
[ 138621-65-5 ]

Reference： [1]Tetrahedron Letters,1991,vol. 32,p. 6327 - 6328
[2]Tetrahedron Letters,1991,vol. 32,p. 6327 - 6328

7
[ 22509-74-6 ]
[ 68208-19-5 ]
[ 167886-86-4 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3238 - 3240

8
[ 64-17-5 ]
[ 68208-19-5 ]
ethyl 3-Amino-3-(3-methoxyphenyl)-propionate hydrochloride [ No CAS ]

Reference： [1]Pharmacy and Pharmacology Communications,1998,vol. 4,p. 231 - 235

10
[ 68208-19-5 ]
[ 210161-79-8 ]

Reference： [1]Pharmacy and Pharmacology Communications,1998,vol. 4,p. 231 - 235

11
[ 68208-19-5 ]
ethyl-3-[3-N'-(2-chloroethyl)-3N'-nitrosoureido]-3-(3-methoxyphenyl)propionate [ No CAS ]

Reference： [1]Pharmacy and Pharmacology Communications,1998,vol. 4,p. 231 - 235

12
[ 68208-19-5 ]
3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-(3-methoxy-phenyl)-propionamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3238 - 3240

13
[ 100-83-4 ]
[ 68208-19-5 ]

Reference： [1]Archiv der Pharmazie,1928,p. 119

14
[ 67-56-1 ]
[ 68208-19-5 ]
[ 669087-27-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; for 7.0h;Heating / reflux;	A solution of beta-amino-3-methoxy-benzenepropanoic acid (WO0041469) (9.38g,52mmol) in concentrated hydrochloric acid (10ml) and methanol (115ml), was heated under reflux for 7 hours, then cooled. The reaction was evaporated under reduced pressure, and the residue partitioned between ethyl acetate (300ml) and 1 N sodium hydroxide solution (300ml). The layers were separated, and the organic phase evaporated under reduced pressure to afford the title compound as a colourless oil, 8.8g. 1H nmr (CDCl3,400MHz 2.77 (m, 4H), 3. 68 (s, 3H), 3.80(s, 3H), 4.42 (t, 1H), 6, 80 (m,1 H), 6. 96 (m, 2H), 7.24 (m,1 H). LRMS: m/z (ES+) 232 [MNa+]

Reference： [1]Patent: WO2004/20414,2004,A1 .Location in patent: Page 100
[2]Journal of Medicinal Chemistry,2010,vol. 53,p. 8619 - 8626

15
[ 68208-19-5 ]
[ 167886-86-4 ]

Yield	Reaction Conditions	Operation in experiment
		Similarly from 3-amino-3-(3-methoxyphenyl)propionic acid there is obtained 3-phthalimido-3-(3-methoxyphenyl)propionic acid as white crystals: mp 111-115 C.; 1 H NMR (dmsod6, 250 MHz) 6 12.5 (br s, 1H), 7.94-7.81 (m, 4 H), 7.32-7.23 (m, 1H), 7.02-6.85 (m, 3 H), 5.70-5.60 (m, 1 H), 3.77-3.67 (s, 3H), 3.56-3.15 (m, 2 H); 13 C NMR (dmso-d6) delta 171.6, 167.6, 159.2, 140.4, 134.7, 131.0, 129.7, 123.2, 119.0, 112.9, 112.7, 54.9, 50.0, 35.8.
		Similarly from 3-amino-3-(3-methoxyphenyl)propionic acid there is obtained 3-phthalimido-3-(3-methoxyphenyl)propionic acid as white crystals: mp 111-115 C.; 1H NMR (DMSO-d6, 250 MHz) delta 12.5 (br s, 1H), 7.94-7.81 (m, 4 H), 7.32-7.23 (m, 1H), 7.02-6.85 (m, 3 H), 5.70-5.60 (m, 1 H), 3.77-3.67 (s, 3H), 3.56-3.15 (m, 2 H); 13C NMR (DMSO-d6) delta 171.6, 167.6, 159.2, 140.4, 134.7, 131.0, 129.7, 123.2, 119.0, 112.9, 112.7, 54.9, 50.0, 35.8.
		Similarly from 3-amino-3-(3-methoxyphenyl)propionic acid there is obtained 3-phthalimido-3-(3-methoxyphenyl)propionic acid as white crystals: mp 111-115 C.; 1H NMR (DMSO-6, 250 MHz) delta12.5 (br s, 1H), 7.94-7.81 (m, 4H), 7.32-7.23 (m, 1H), 7.02-6.85 (m, 3H), 5.70-5.60 (m, 1H), 3.77-3.67 (s, 3H), 3.56-3.15 (m, 2H); 13C NMR (DMSO-d6) delta171.6, 167.6, 159.2, 140.4, 134.7, 131.0, 129.7, 123.2, 119.0, 112.9, 112.7, 54.9, 50.0, 35.8.

Reference： [1]Patent: US5463063,1995,A
[2]Patent: US5605914,1997,A
[3]Patent: US5698579,1997,A

16
[ 591-31-1 ]
[ 68208-19-5 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium acetate;	3-Amino-3-(3-methoxyphenyl)-propionic acid (8a): Corresponding to Example 1a, 200 g of 3-methoxybenzaldehyde were reacted with ammonium acetate and malonic acid. A white solid was obtained (yield: 135.5 g). 1H-NMR (400 MHz, D1-trifluoroacetic acid): 3.31 (dd, 1H), 3.54 (dd, 1H), 4.03 (s, 3H), 5.00 (m, 1H), 7.19 (m, 3H), 7.52 (t, 1H).

Reference： [1]Patent: US6291503,2001,B1

17
[ 68208-19-5 ]
ethyl 3-Amino-3-(3-methoxyphenyl)-propionate hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In ethanol;	Ethyl 3-Amino-3-(3-methoxyphenyl)-propionate hydrochloride (8b): Corresponding to Example 1b, 60 g of (8a) were treated with hydrochloric acid in ethanol. A white, crystalline product was obtained (yield: 75 g). 1H-NMR (400 MHz, D4-MeOH): 1.17 (t, 3H), 3.01 (dd, 1H), 3.14 (dd, 1H), 3.82 (s, 3H), 4.14 (m, 2H), 4.70(m, 1H), 6.98 (d, 1H), 7.06 (m, 2H), 7.37 (t, 1H).

Reference： [1]Patent: US6291503,2001,B1

18
[ 68208-19-5 ]
[ 76-05-1 ]
[ 407-25-0 ]
[ 138621-65-5 ]

Yield	Reaction Conditions	Operation in experiment
	for 3.25h;Heating / reflux;	A solution of <strong>[68208-19-5]3-amino-3-(3-methoxyphenyl)propanoic acid</strong> (2.0 g, 10.0 mmol) in trifluoro acetic acid (15 mL) was stirred for 15 minutes. Trifiuoro acetic anhydride (15 mL) was added and the reaction mixture was heated to reflux for 3 hours. The volatiles were removed in vacuo, the residue was triturated with water and the resulting yellow solid was collected by vacuum filtration. Recrystallization with diethyl ether yielded 2,2,2-trifiuoro-N-(6-methoxy-3-oxo-2,3-dihydro-lH-inden-l-yl)acetamide (1.3 g, 4.8 mmol). 1H-NMR (300 MHz, DMSOd6) delta ppm: 9.95 (bd, IH), 7.62 (m, IH), 7.05 (m, 2H), 5.60 (m, IH), 3.88 (s, 3H), 3.05 (dd, IH), 2.55 (m, IH).

Reference： [1]Patent: WO2009/16241,2009,A1 .Location in patent: Page/Page column 44

19
[ 68208-19-5 ]
C₃₂H₄₃BN₂O₅ [ No CAS ]