306937-12-2|3-((tert-Butoxycarbonyl)amino)-4-methoxybenzoic acid| Ambeed

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Quality Control of [ 306937-12-2 ] Purity: 97% SDS Specification

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Product Details of [ 306937-12-2 ]

CAS No. :	306937-12-2
Formula :	C₁₃H₁₇NO₅
M.W :	267.28
SMILES Code :	O=C(O)C1=CC=C(OC)C(NC(OC(C)(C)C)=O)=C1
MDL No. :	MFCD01765428
Boiling Point :	No data available
InChI Key :	HJRQIHYNWZEWHF-UHFFFAOYSA-N
Pubchem ID :	2735632

Safety of [ 306937-12-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 306937-12-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	19
Num. arom. heavy atoms	6
Fraction Csp3	0.38
Num. rotatable bonds	6
Num. H-bond acceptors	5.0
Num. H-bond donors	2.0
Molar Refractivity	70.14
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	84.86 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.55
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	2.69
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.55
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.	1.69
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	1.23
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.14

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.03
Solubility	0.25 mg/ml ; 0.000934 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.12
Solubility	0.0201 mg/ml ; 0.000075 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-2.85
Solubility	0.376 mg/ml ; 0.00141 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	Yes
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.	-6.02 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<0.0
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)	2.49

Application In Synthesis of [ 306937-12-2 ]

* 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 [ 306937-12-2 ]

[ 306937-12-2 ] Synthesis Path-Downstream 1~25

1
[ 24424-99-5 ]
[ 2840-26-8 ]
[ 306937-12-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydroxide; In tetrahydrofuran; at 20℃; for 12.5h;Cooling with ice;	3-Amino-p-anisic acid (1) (20.0 g,119 mmol)was suspended in asolution of NaOH (1 mol/L, 180 mL) and THF (150 mL). The mixturewas cooled in an ice bath. A solution of di-tert-butyl dicarbonate(Boc)2O (104.4 g, 479 mmol) in THF (70 mL) was then addeddropwise over a period of 30 min under stirring. The ice-bath wasremoved after dropping and the mixture was stirred for another12 h at room temperature. Thereafter, the THF was removed invacuo, and the remaining aqueous solution was diluted with water.The resulting mixture was extracted three times with AcOEt(70mL 3). The aqueous layer was acidified with concentrated HClto neutralize PH to 4e5 and extracted with AcOEt (80 mL 3). Thecombined organic layers were washed with water, and dried overNa2SO4. Then filtration and concentration in vacuo gave (2) (20.78 g,65%) as off-white solid, which was used for the next step withoutfurther purification.
65%	With sodium hydroxide; In tetrahydrofuran; at 20℃; for 5.0h;Cooling with ice;	20 g of 3-amino-4-methoxybenzoic acid (Compound 1) was dissolved in 180 ml of sodium hydroxide solution, 150 ml of tetrahydrofuran was added thereto, and a solution of BOC anhydride (104,4 g) in tetrahydrofuran (70 ml) was added dropwise to the ice bath The ice bath was removed and stirred at room temperature for 5 hours. After the completion of the stirring, the product was extracted with 80 ml of ethyl acetate, and the organic phase was combined and washed with saturated sodium chloride, and the mixture was washed with anhydrous sulfuric acid Sodium dry.Rotate the liquid to give 20.78 g of an off-white solid 3 - ((tert-butoxycarbonyl) amino) -4-methoxybenzoic acid (Compound 2) in 65% yield;
50%		1) 1.0 g (6 mmol) 3-amino-4-methoxybenzoic acid is dissolved in 10 ml 4N NaOH aqueous solution, 2.5 ml (11 mmol) tert-butyric anhydride is slowly dropped into the solution. The mixture is heated up to 50 C. until the reaction finishes and the resulted alkaline solution is quickly acidified to pH=2 using 1 N hydrochloric acid and extracted three times using chloroform. The chloroform extract is pooled and desiccated with anhydrate sodium sulfate, subsequently condensed to dryness to obtain 0.8 g off- white solid, yield: 50%.

References: [1]European Journal of Organic Chemistry,2001,p. 311 - 322.
[2]European Journal of Medicinal Chemistry,2015,vol. 103,p. 80 - 90.
[3]Patent: CN104817489,2017,B .Location in patent: Paragraph 0037-0040.
[4]Patent: US2011/178108,2011,A1 .Location in patent: Page/Page column 17.

2
[ 100-39-0 ]
[ 306937-12-2 ]
[ 330807-52-8 ]

References: [1]European Journal of Organic Chemistry,2001,p. 311 - 322.

3
[ 306937-12-2 ]
[ 167993-22-8 ]

References: [1]European Journal of Organic Chemistry,2001,p. 311 - 322.

4
[ 306937-12-2 ]
Boc-(L)-Pro-AB(4-OCH₃)-OBn [ No CAS ]

References: [1]European Journal of Organic Chemistry,2001,p. 311 - 322.

5
[ 24313-88-0 ]
[ 306937-12-2 ]
[ 1131314-64-1 ]

Yield	Reaction Conditions	Operation in experiment
55.6%		2) 200 mg (0.8 mmol) of the product from step 1) is mixed with 120 mg (0.9 mmol) HOBT and 0.06 ml (0.6 mmol) DIC in dry DMF under ice-water bath condition. The mixture is stirred for 30 min. under N2 protection, then 160 mg (0.9 mmol) 3,4,5-trimethoxyaniline is subsequently added, the mixture is let to naturally resume room temperature and stirred overnight. The resulted reactant is evaporated to dryness under reduced pressure, the residue is dissolved in ethyl acetate and subsequently filtered, the filtrate is evaporated to dryness, separated using preparatory thin layer silica plate to obtain 180 mg product, yield: 55.6%.

References: [1]Patent: US2011/178108,2011,A1 .Location in patent: Page/Page column 17.

6
[ 306937-12-2 ]
[ 1131312-67-8 ]

References: [1]Patent: US2011/178108,2011,A1 .

7
(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide [ No CAS ]
[ 306937-12-2 ]
[ 1610861-49-8 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃;	Step 1: Synthesis of (S)-4-(2-(3-(tert-butoxycarbonylamino)-4-methoxybenzoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (198) [0566] Compound 3 (500 mg, 1.2 mmol) and <strong>[306937-12-2]3-(tert-butoxycarbonylamino)-4-methoxybenzoic acid</strong> (481 mg, 1.8 mmol) were dissolved in DMF (5 ml). DMAP (176 mg, 1.44 mmol) and EDC (690 mg, 3.6 mmol) were added, and the mixture was stirred at RT over night. The reaction was diluted with water and extracted with ethyl acetate. The organic phase was washed with HCl 1N (2×), NaHCO3 saturated solution and brine, dried over Na2SO4 and evaporated under vacuum to yield 650 mg of crude, that was used for the next step without any further purification.

References: [1]Patent: US2014/155391,2014,A1 .Location in patent: Paragraph 0565; 0566.

8
[ 306937-12-2 ]
[ 1610861-41-0 ]