[ CAS No. 134978-97-5 ] {[proInfo.proName]}

Name: 134978-97-5|2-(2-(2-Aminoethoxy)ethoxy)acetic acid|95%
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SKU: A158309
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Quality Control of [ 134978-97-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 134978-97-5 ]

CAS No. :	134978-97-5	MDL No. :	MFCD13185897
Formula :	C₆H₁₃NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RUVRGYVESPRHSZ-UHFFFAOYSA-N
M.W :	163.17	Pubchem ID :	362706
Synonyms :

Calculated chemistry of [ 134978-97-5 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.83
Num. rotatable bonds :	7
Num. H-bond acceptors :	5.0
Num. H-bond donors :	2.0
Molar Refractivity :	37.61
TPSA :	81.78 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) :	-9.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.18
Log Po/w (XLOGP3) :	-3.7
Log Po/w (WLOGP) :	-0.94
Log Po/w (MLOGP) :	-1.29
Log Po/w (SILICOS-IT) :	-0.52
Consensus Log Po/w :	-1.05

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	1.94
Solubility :	14300.0 mg/ml ; 87.4 mol/l
Class :	Highly soluble
Log S (Ali) :	2.57
Solubility :	60800.0 mg/ml ; 372.0 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.39
Solubility :	66.5 mg/ml ; 0.407 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.19

Safety of [ 134978-97-5 ]

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 [ 134978-97-5 ]

* 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 [ 134978-97-5 ]
Downstream synthetic route of [ 134978-97-5 ]

[ 134978-97-5 ] Synthesis Path-Upstream 1~6

1
[ 166108-70-9 ]
[ 134978-97-5 ]

Reference： [1] Organic Letters, 2005, vol. 7, # 9, p. 1699 - 1702

2
[ 882518-90-3 ]
[ 134978-97-5 ]

Reference： [1] Organic and Biomolecular Chemistry, 2008, vol. 6, # 17, p. 3065 - 3078

3
[ 166108-71-0 ]
[ 134978-97-5 ]

Reference： [1] Patent: WO2006/82245, 2006, A1, . Location in patent: Page/Page column 357
[2] Journal of the American Chemical Society, 2011, vol. 133, # 40, p. 16235 - 16242

4
[ 108466-89-3 ]
[ 134978-97-5 ]

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 23, p. 6567 - 6572

5
[ 24424-99-5 ]
[ 134978-97-5 ]
[ 108466-89-3 ]

Yield	Reaction Conditions	Operation in experiment
62.1%	With sodium carbonate In 1,4-dioxane; water at 20℃; for 12 h;	Step 3a: To a stirred solution of compound 1a (5.0 g, 30.6 mmol) in 1,4-Dioxane (50 mL), Sodium carbonate (8.12 g, 76.5 mmol, dissolved in 10 mL water) and (Boc)₂O (9.98 mL, 45.7 mmol) were added and stirred at room temperature for 12 h. The progress of reaction was monitored by TLC. The reaction mass was partitioned between diethyl ether and water. Then aqueous layer was made acidic (pH=3) by 3N HCl solution and was extracted with DCM (2×200 mL). Organic layer was washed with water, brine, dried over Na₂SO₄and evaporated under reduced pressure to yield 50 g of pure 3a (Yield: 62.1percent). LCMS: 263.0 (M+H)⁺
62.1%	With sodium carbonate In 1,4-dioxane; water at 20℃; for 12 h;	To a stirred solution of compound la (5.0 g, 30.6 mmol) in 1,4-Dioxane (50 mL), Sodium carbonate (8.12 g, 76.5 mmol, dissolved in 10 mL water) and (Boc)20 (9.98 mL, 45.7 mmol) were added and stirred at room temperature for 12 h. The progress ofreaction was monitored by TLC. The reaction mass was partitioned between diethyl ether and water. Then aqueous layer was made acidic (pH = 3) by 3N HC1 solution and was extracted with DCM (2 x 200 mL). Organic layer was washed with water, brine, dried over Na2504 and evaporated under reduced pressure to yield 50 g of pure 3a (Yield:62.1percent). LCMS: 263.0 (M+H).

Reference： [1] Organic and Biomolecular Chemistry, 2008, vol. 6, # 17, p. 3065 - 3078
[2] Patent: US2015/73042, 2015, A1, . Location in patent: Paragraph 0150; 0151
[3] Patent: WO2015/33303, 2015, A1, . Location in patent: Page/Page column 26; 27

6
[ 82911-69-1 ]
[ 134978-97-5 ]
[ 166108-71-0 ]

Reference： [1] Organic Letters, 2005, vol. 7, # 9, p. 1699 - 1702

[ 134978-97-5 ] Synthesis Path-Downstream 1~86

1
[ 166108-70-9 ]
[ 134978-97-5 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 1699 - 1702

2
[ 82911-69-1 ]
[ 134978-97-5 ]
[ 166108-71-0 ]

Yield	Reaction Conditions	Operation in experiment
200 g	With hydrogenchloride; In ethanol; water;pH 9.0;	In a 3000L three-necked flask equipped with mechanical stirring, condenser and constant pressure dropping funnel,330 g of crude product (Intermediate 3) was dissolved in 1000 ml of ethanol, and 350 g of 30% NaOH solution was added dropwise.After the completion of the dropwise addition, the mixture was heated to reflux, and monitored by TLC, the intermediate 3 was completely disappeared, and the temperature was lowered. The pH was adjusted to 9 with hydrochloric acid, and a solution of 337 g of Fmoc-Osu in 1000 ml of ethanol was added dropwise.If the pH has dropped, add sodium bicarbonate and keep it at around 8.TLC was monitored until Intermediate 4 disappeared. The pH was adjusted to 1-2 with hydrochloric acid, the ethanol was distilled off, 1000 ml of water was added, and the mixture was extracted three times with ethyl acetate 500*3, and washed twice with saturated brine.The ethyl acetate was concentrated to give 285 g of crude material.Recrystallization from 1000 ml of ethyl acetate gave 200 g of product[2-[1-(Fmoc-Amino)ethoxy]ethoxy]acetic acid, yield 51.9%.

Reference： [1]Organic Letters,2005,vol. 7,p. 1699 - 1702
[2]Patent: CN110078644,2019,A .Location in patent: Paragraph 0065; 0068; 0070-0071; 0074; 0076

3
[ 134978-97-5 ]
N-(3-{2-[2-(3-{2-[2-(2-{6-[eicosa-5,8,11,14-tetraenoyl-(4-hydroxy-3-methoxy-benzyl)-amino]-hexanoylamino}-ethoxy)-ethoxy]-acetylamino}-propoxy)-ethoxy]-ethoxy}-propyl)-3-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-succinamic acid [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 1699 - 1702

4
[ 134978-97-5 ]
C₇₀H₁₁₄N₈O₁₈S [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 1699 - 1702

5
[ 166108-71-0 ]
[ 134978-97-5 ]

Yield	Reaction Conditions	Operation in experiment
	With PS-trisamine resin; In N,N-dimethyl-formamide;	The title compound was prepared by coupling of 4-[3-(2H-tetrazol-5-yl)carbazol-9- ylmethyl]benzoic acid 2,5-dioxopyrrolidin-1 -yl ester with [2-(2-aminoethoxy)ethoxy]acetic acid (prepared from [2-[2-(Fmoc-amino)ethoxy]ethoxy]acetic acid by treatment with PS-Trisamine resin in DMF). HPLC-MS (Method C): m/z: 515 (M+1 ); Rt = 3.10 min.

Reference： [1]Patent: WO2006/82245,2006,A1 .Location in patent: Page/Page column 357
[2]Journal of the American Chemical Society,2011,vol. 133,p. 16235 - 16242

6
[ 873694-43-0 ]
[ 134978-97-5 ]
[ 720695-95-4 ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was prepared by coupling of 4-[3-(2H-tetrazol-5-yl)carbazol-9- ylmethyl]benzoic acid 2,5-dioxopyrrolidin-1 -yl ester with <strong>[134978-97-5][2-(2-aminoethoxy)ethoxy]acetic acid</strong> (prepared from [2-[2-(Fmoc-amino)ethoxy]ethoxy]acetic acid by treatment with PS-Trisamine resin in DMF). HPLC-MS (Method C): m/z: 515 (M+1 ); Rt = 3.10 min.

Reference： [1]Patent: WO2006/82245,2006,A1 .Location in patent: Page/Page column 356; 357

7
sodium 8-acetylamino-3,6-dioxaoctanoate [ No CAS ]
[ 134978-97-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; In ethanol; water; ethyl acetate;	A2.2 8-Amino-3,6-dioxaoctanoic acid 63.5 g of sodium 8-acetylamino-3,6-dioxaoctanoate were dissolved in 200 ml of water. 11.2 g of NaOH were added at 20 C., and the reaction mixture was then heated at 100 C. for 8 h until precursor was no longer detectable. The pH was then adjusted to 6 with 53.7g of 37% by weight aqueous hydrochloric acid, and the solvent was distilled off under reduced pressure. The oily residue was dissolved in 200 ml of ethanol and filtered to remove undissolved sodium chloride, the mother liquor was slowly added dropwise to 1 l of ethyl acetate, and the oily phase which separated out was removed and dried under reduced pressure. This resulted in 40.6 g of 8-amino-3,6-dioxaoctanoic acid (corresponding to 89% of theory).

Reference： [1]Patent: US5907055,1999,A

8
[ 882518-90-3 ]
[ 134978-97-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 3065 - 3078

9
[ 24424-99-5 ]
[ 134978-97-5 ]
[ 108466-89-3 ]

Yield	Reaction Conditions	Operation in experiment
62.1%	With sodium carbonate; In 1,4-dioxane; water; at 20℃; for 12h;	Step 3a: To a stirred solution of compound 1a (5.0 g, 30.6 mmol) in 1,4-Dioxane (50 mL), Sodium carbonate (8.12 g, 76.5 mmol, dissolved in 10 mL water) and (Boc)2O (9.98 mL, 45.7 mmol) were added and stirred at room temperature for 12 h. The progress of reaction was monitored by TLC. The reaction mass was partitioned between diethyl ether and water. Then aqueous layer was made acidic (pH=3) by 3N HCl solution and was extracted with DCM (2×200 mL). Organic layer was washed with water, brine, dried over Na2SO4 and evaporated under reduced pressure to yield 50 g of pure 3a (Yield: 62.1%). LCMS: 263.0 (M+H)+
62.1%	With sodium carbonate; In 1,4-dioxane; water; at 20℃; for 12h;	To a stirred solution of compound la (5.0 g, 30.6 mmol) in 1,4-Dioxane (50 mL), Sodium carbonate (8.12 g, 76.5 mmol, dissolved in 10 mL water) and (Boc)20 (9.98 mL, 45.7 mmol) were added and stirred at room temperature for 12 h. The progress ofreaction was monitored by TLC. The reaction mass was partitioned between diethyl ether and water. Then aqueous layer was made acidic (pH = 3) by 3N HC1 solution and was extracted with DCM (2 x 200 mL). Organic layer was washed with water, brine, dried over Na2504 and evaporated under reduced pressure to yield 50 g of pure 3a (Yield:62.1%). LCMS: 263.0 (M+H).

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 3065 - 3078
[2]Patent: US2015/73042,2015,A1 .Location in patent: Paragraph 0150; 0151
[3]Patent: WO2015/33303,2015,A1 .Location in patent: Page/Page column 26; 27

10
[ 134978-97-5 ]
[ 77-76-9 ]
(2-(2-aminoethoxy)ethoxy)acetic acid methyl ester [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 3065 - 3078

Yield	Reaction Conditions	Operation in experiment
		Xa is selected among the following amino acid residues: ... arginine; ornithine; tranexamic acid; N-methyl-tranexamic acid; 8-amino-3,6-dioxaoctanoic acid; 4(piperidin-4-yl)butanoic acid; 3(piperidin-4-yl)propionic acid; N-(4-aminobutyl)-glycine; ...
		...of the following groups: -(Gly)n-, n ranging from 1 to 10; -(Pro)n-, n ranging from 1 to 10; NH2-(CH2)n-COON, n ranging from 1 to 10; NH2-(CH2-CH2-O)m-CH2CH2COOH, m ranging from 3 to 6; 8-amino-3,6-dioxaoctanoic acid; tranexamic acid; N-methyl-tranexamic acid; 4(piperidin-4-yl)butanoic acid; 3(piperidin-4-yl)propionic acid; N-(4-aminobutyl)-glycine; 4-carboxymethyl-piperazine; 4-(4-aminophenyl)butanoic acid; ...
		...ing amino acid residues: -(Gly)n-, n ranging from 1 to 10; -(Pro)n-, n ranging from 1 to 10; NH2-(CH2)n-COON, n ranging from 1 to 10; NH2-(CH2-CH2-O)m-CH2CH2COOH, m ranging from 3 to 6; 8-amino-3,6-dioxaoctanoic acid; tranexamic acid; N-methyl-tranexamic acid; 4(piperidin-4-yl)butanoic acid; 3(piperidin-4-yl)propionic acid; N-(4-aminobutyl)-glycine; 4-carboxymethyl-piperazine; 4-(4-aminophenyl)butanoic acid; ...

		Xe is chosen from the following amino acid residues: NH2-(CH2)-COOH, n varying from 1 to 10; NH2-(CH2-CH2-O)m-CH2CH2COOH, m varying from 3 to 6; 8-amino-3,6-dioxaoctanoic acid; tranexamic acid; N-methyl-tranexamic acid; 4(piperidin-4-yl)butanoic acid; 3(piperidin-4-yl)propionic acid; N-(4-aminobutyl)-glycine; 4-carboxymethyl-piperazine; 4-(4-aminophenyl)butanoic acid; ...
		Xg corresponding to the residue of one of the following groups: -NH2-(CH2)g-COOH, n varying from 1 to 10; -NH2-(CH2-CH2-O)m-CH2CH2COOH, m varying from 3 to 6; 8-amino-3,6-dioxaoctanoic acid; tranexamic acid; N-methyl-tranexamic acid; 4(piperidin-4-yl)butanoic acid; 3(piperidin-4-yl)-propionic acid; N-(4-aminobutyl)-glycine; 4-carboxymethyl-piperazine; 4-(4-aminophenyl)butanoic acid; ...
		Xg corresponding to the residue of one of the following groups: -NH2-(CH2)-COOH, n varying from 1 to 10; -NH2-(CH2-CH2-O)mCH2CH2COOH, m varying from 3 to 6; 8-amino-3,6-dioxaoctanoic acid; tranexamic acid; N-methyl-tranexamic acid; 4(piperidin-4-yl)butanoic acid; 3(piperidin-4-yl)-propionic acid; N-(4-aminobutyl)-glycine; 4-carboxymethyl-piperazine; 4-(4-aminophenyl)butanoic acid; ...
		Xf is chosen from the following amino acid residues: NH2-(CH2)-COOH, n varying from 1 to 10; NH2-(CH2-CH2-O)m-CH2CH2COOH, m varying from 3 to 6; 8-amino-3,6-dioxaoctanoic acid; tranexamic acid; N-methyl-tranexamic acid; 4(piperidin-4-yl)butanoic acid; 3(piperidin-4-yl)propionic acid; N-(4-aminobutyl)-glycine; 4-carboxymethyl-piperazine; 4-(4-aminophenyl)butanoic acid; ...
		Xc is chosen from the following amino acid residues: ... trans-4-aminocyclohexane acetic acid; 4-amino-1-carboxymethyl piperidine; 4-aminobenzoic acid; 4(2-aminoethoxy)benzoic acid; 8-amino-3,6-dioxaoctanoic acid; tranexamic acid; N-methyl-tranexamic acid; 4(piperidin-4-yl)butanoic acid; ...

12
[ 138-41-0 ]
[ 134978-97-5 ]
[ 1335096-02-0 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 16235 - 16242

13
[ 134978-97-5 ]
C₅₆H₈₉N₁₁O₂₁S [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 16235 - 16242

14
C₈₂H₁₁₆N₁₀O₂₁ [ No CAS ]
[ 134978-97-5 ]
C₈₈H₁₂₇N₁₁O₂₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; pivaloyl chloride; N-ethyl-N,N-diisopropylamine; trimethylsilylacetamide; In dichloromethane; N,N-dimethyl acetamide; at -5 - 20℃;	8.9 g HOOCCH2OCH2C(O)-Phe-Glu(OtBu)-Phe-Lys(Boc)-Phe-Glu(OtBu)-Phe-Lys(Boc)-OEt (SEQ ID NO:101) (5.6 mmol), 1.15 ml diisopropylethylamine (5.68 mmol) and 0.47 ml pyridine (5.68 mmol) were dissolved in a mixture of 70 ml N,N-dimethylacetamide and 20 ml dichloromethane. The reaction mixture was cooled to -5C (solution n1). 1.02 g 8-amino-3,6-dioxaoctanoic acid (6.19 mmol) was dispersed in 2.30 ml dichloromethane containing 1.84 g trimethylsilylacetamide (12.4 mmol) (solution n2). Solution n2 was stirred at room temperature and then cooled to 10C. At -5C, 0.7 g pivaloyl chloride was added to solution n1. After about 5 min of further stirring, cooled solution n2 was added to solution n1. The reaction mixture was allowed to warm to room temperature. After controlling the completion of the reaction by HPLC, 2 ml water was added, the reaction mixture partially concentrated under vacuum and then poured into a solution of KHS04 (2.5 g) in 500 ml water. The resulting precipitate was filtered, washed with water (50 ml) twice and then dried under vacuum at 45C. After drying, 9.17 g (94 %) of an off-white product was obtained. The HPLC analysis of the product was carried out as follows : a sample was dissolved in 1 ml N,N-dimethylacetamide and analysed using method CH-GS-10 ; tR = 7.8 ± 0.5 min. Product purity : 89 % of surface area (HPLC).

Reference： [1]Patent: EP2692361,2014,A1 .Location in patent: Paragraph 0042

15
[ 134978-97-5 ]
C₂₆H₄₉N₇O₁₁ [ No CAS ]