143766-89-6|N-Boc-Iminodipropionic acid| Ambeed

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Quality Control of [ 143766-89-6 ] Purity: 97% SDS Specification

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Product Details of [ 143766-89-6 ]

CAS No. :	143766-89-6
Formula :	C₁₁H₁₉NO₆
M.W :	261.27
SMILES Code :	O=C(N(CCC(O)=O)CCC(O)=O)OC(C)(C)C
MDL No. :	MFCD11226793
InChI Key :	NIFJJASPEGEHDS-UHFFFAOYSA-N
Pubchem ID :	15666718

Safety of [ 143766-89-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 143766-89-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	18
Num. arom. heavy atoms	0
Fraction Csp3	0.73
Num. rotatable bonds	9
Num. H-bond acceptors	6.0
Num. H-bond donors	2.0
Molar Refractivity	63.14
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	104.14 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.7
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.11
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.17
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.52
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.13
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.67

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.94
Solubility	30.3 mg/ml ; 0.116 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.85
Solubility	3.67 mg/ml ; 0.0141 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.49
Solubility	85.3 mg/ml ; 0.327 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.82 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.4

Application In Synthesis of [ 143766-89-6 ]

* 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 [ 143766-89-6 ]

[ 143766-89-6 ] Synthesis Path-Downstream 1~30

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[ 143766-89-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium hydroxide; In tetrahydrofuran; water; at 4℃; for 3.0h;	To a solution of 3, 3'-azanediyldipropanoic acid (10.00 g, 62.08 mmol) in 1.0 M NaOH (300 ml) at 4 was added di-tert-butyl dicarbonate (22.10 g, 101.3 mmol) in 200 ml THF in 1 h. After addition, the mixture was kept to stirring for 2 h at 4 . The mixture was carefully acidified to pH 4 with 0.2 M H 3PO 4, concentrated in vacuo, extracted with CH2Cl2, dried over Na2SO4, evaporated and purified with flash SiO2 chromatography eluted with AcOH/MeOH/CH 2Cl 2 (0.01: 1: 5) to afford 3, 3'- ( (tert-butoxycarbonyl) azanediyl) dipropanoic acid (13.62 g, 84%yield) . ESI MS m/z C 11H 19NO 6 [M+H] +, cacld. 262.27, found 262.40.
84%	With sodium hydroxide; In tetrahydrofuran; water; at 4℃; for 3.0h;	To a solution of 3, 3'-azanediyldipropanoic acid (10.00 g, 62.08 mmol) in 1.0 M NaOH (300 ml) at 4 was added di-tert-butyl dicarbonate (22.10 g, 101.3 mmol) in 200 ml THF in 1 h. After addition, the mixture was kept to stirring for 2 h at 4 . The mixture was carefully acidified to pH 4 with 0.2 M H 3PO 4, concentrated in vacuo, extracted with CH2Cl2, dried over Na2SO4, evaporated and purified with flash SiO2 chromatography eluted with AcOH/MeOH/CH 2Cl 2 (0.01: 1: 5) to afford 3, 3'- ( (tert-butoxycarbonyl) azanediyl) dipropanoic acid (13.62 g, 84%yield) . ESI MS m/z C 11H 19NO 6 [M+H] +, cacld. 262.27, found 262.40. [0361] To a solution of 3, 3'- ( (tert-butoxycarbonyl) azanediyl) dipropanoic acid (8.0 g, 30.6 mmol) in CH 2Cl 2 (500 ml) at 0 was added phosphorus pentoxide (8.70 g, 61.30 mmol) . The mixture was stirred at 0 for 2 h and then r.t. for 1 h, filtered through short SiO 2 column, and rinsed the column with EtOAc/CH 2Cl 2 (1: 6) . The filtrate was concentrated and triturated with EtOAc/hexane to afford the title compound (5.64 g, 74%yield) . ESI MS m/z C 11H 17NO 5 [M+H] +, cacld. 244.11, found 244.30.
84%	With sodium hydroxide; In tetrahydrofuran; water; at 4℃; for 3.0h;	To a solution of 3,3'-iminodipropionic acid (10.00g, 62.08mmol) in 1.0N NaOH (300mL) at 4 C, di-tert-butyl dicarbonate (22.10g, 101.3mmol) in tetrahydrofuran ( 200 mL) solution.After 1 hour of addition, the mixture was stirred at 4 C for 2 hours. The mixture was carefully acidified to pH 4 with 0.2M H3PO4,Concentrated under reduced pressure,Extracted with dichloromethane,Dried over sodium sulfate, filtered,After concentration, it was purified by silica gel column.Eluted with AcOH / MeOH / CH2Cl2 (0.01: 1: 5),3,3 '-((tert-butoxycarbonyl) imino) dipropionic acid was obtained (13.62 g, yield 84%).

84%	With sodium hydroxide; In tetrahydrofuran; at 4℃; for 3.0h;	At 4C, to 3,3'-iminodipropionic acid (10.00g, 62.08mmol) in 1.0N NaOH (300ml) solution was added di-tert-butyl dicarbonate (22.10g, 101.3mmol) in 200ml THF solution. After 1 hour of addition, the mixture was stirred at 4 C for 2 hours. The mixture was carefully acidified to pH-4 with 0.2M H3PO4, concentrated in vacuo, extracted with methane, dried over sodium sulfate, concentrated and purified with a silica gel column.It was eluted with AcOH/MeOH/CH2Cl2 (0.01:1:5) to obtain 3,3'-((tert-butoxycarbonyl)imino)dipropionic acid (13.62g, yield 84%).
79%	With sodium hydrogencarbonate; In methanol; at 20℃; for 72.0h;	A mixture of 3,3'-iminodipropionic acid (2.79 g, 17.3 mmol), di-tert-butyl dicarbonate (3.78 g, 17.3 mmol), sodium bicarbonate (2.91 g, 34.6 mmol) in methanol (80 mL) was stirred at room temperature for 3 days. The solvent was removed under reduced pressure. Water (60 mL) was added to the residue, and the resulting solution was washed with diethyl ether (100 mL). The aqueous solution was adjusted to pH 3 with 2 N HCl. The acidic solution was extracted with ethyl acetate (100 mL × 2). The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to yield 4 as colorless oil (3.57 g, 79%). 1H NMR (400 MHz, CDCl3) δ 3.53 (t, J = 6.3 Hz, 4H), 2.73 - 2.46 (m, 4H), 1.45 (s, 9H). MS (ESI) calculated for C11H11NO6 261.1, found [M + Na]+ 284.4.

References: [1]Patent: WO2019/127607,2019,A1 .Location in patent: Page/Page column 154.
[2]Patent: WO2020/6722,2020,A1 .Location in patent: Page/Page column 122.
[3]Patent: CN110621673,2019,A .Location in patent: Paragraph 0470-0472.
[4]Patent: WO2020/73345,2020,A1 .Location in patent: Page/Page column 181-182.
[5]Patent: WO2020/155017,2020,A1 .Location in patent: Page/Page column 160.
[6]Patent: WO2020/257998,2020,A1 .Location in patent: Page/Page column 269.
[7]Patent: TW2020/41237,2020,A .Location in patent: Paragraph 000216; 000217.
[8]Patent: WO2021/212638,2021,A1 .Location in patent: Page/Page column 201.
[9]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 708 - 712.
[10]Journal of the Chemical Society. Perkin transactions I,1992,p. 1623 - 1630.

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References: [1]Journal of the Chemical Society. Perkin transactions I,1992,p. 1623 - 1630.

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References: [1]Journal of the Chemical Society. Perkin transactions I,1992,p. 1623 - 1630.

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