313490-25-4|2-((tert-Butoxycarbonyl)amino)-2-(2-chlorophenyl)acetic acid| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 313490-25-4 ] Purity: 98% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 313490-25-4 ]

CAS No. :	313490-25-4
Formula :	C₁₃H₁₆ClNO₄
M.W :	285.72
SMILES Code :	CC(C)(C)OC(=O)NC(C(O)=O)C1=CC=CC=C1Cl
MDL No. :	MFCD03426362
InChI Key :	XPFJZGJBRMTXCE-UHFFFAOYSA-N
Pubchem ID :	2756779

Safety of [ 313490-25-4 ]

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

Computational Chemistry of [ 313490-25-4 ] 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	4.0
Num. H-bond donors	2.0
Molar Refractivity	71.55
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	75.63 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.43
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	2.85
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.67
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.	2.23
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	1.9
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.42

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.24
Solubility	0.163 mg/ml ; 0.000569 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.	-4.1
Solubility	0.0229 mg/ml ; 0.00008 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	-3.38
Solubility	0.119 mg/ml ; 0.000415 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	Yes
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.	-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)	2.78

Application In Synthesis of [ 313490-25-4 ]

* 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 [ 313490-25-4 ]

[ 313490-25-4 ] Synthesis Path-Downstream 1~13

1
[ 313490-25-4 ]
[ 75-08-1 ]
[ 1021948-12-8 ]

References: [1]Advanced Synthesis and Catalysis,2007,vol. 349,p. 1345 - 1348.

2
[ 313490-25-4 ]
[ 1092069-34-5 ]
[ 1092069-94-7 ]

Yield	Reaction Conditions	Operation in experiment
	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20.0℃;Molecular sieve;	HBTU (6.37 g, 16.80 mmol) is added to a solution of intermediate 38 (prepared according to A4.d-1), 2-chloro-α-[[(l,l-dimethylethoxy)carbonyl]amino]- benzeneacetic acid (4.00 g; 14. mmol), DIPEA (9.3 ml; 56 mmol) in DMF dried on molecular sieves (100 ml). The reaction mixture was stirred at room temperature overnight. The reaction was evaporated to yield 22.53g. The product was purified by reversed-phase high-performance liquid chromatography (Shandon Hyperprep Cl 8 BDS (Base Deactivated Silica) 8 μm, 250 g, LD. 5 cm). A gradient with 2 phases was applied. Phase A: a 0.25 % NH4HCO3 solution in water; phase B: CH3CN). The desired fractions were collected and worked-up. After partial evaporation at 30-35 0C, extraction with CH2Cl2 (2 x 400 ml) followed by EtOAc extraction (300 ml), drying (MgSO4) and work up of the organic phases, 4512 mg residue was obtained from CH2Cl2 and 45 mg from EtOAc. Yield: 4512 mg (54.3 %) (mixture of R and S- enantiomers). This fraction was separated on SFC (column OJ-H, 30 % CH3OH containing 0.2 % isopropylamine) into its enantiomers. Fraction A yielded 1780 mg (R* enantiomer) and fraction B yielded 1770 mg of intermediate 79 (S* enantiomer).

References: [1]Patent: WO2008/148868,2008,A1 .Location in patent: Page/Page column 97.

3
[ 67-56-1 ]
[ 313490-25-4 ]
[ 1253091-76-7 ]

References: [1]Tetrahedron Asymmetry,2010,vol. 21,p. 2136 - 2141.

4
[ 24424-99-5 ]
2-amino-(2-chlorophenyl)ethanoic acid [ No CAS ]
[ 313490-25-4 ]

References: [1]Tetrahedron Asymmetry,2010,vol. 21,p. 2136 - 2141.

5
[ 313490-25-4 ]
[ 109-85-3 ]
[ 1366062-98-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20.0℃; for 2.0h;	Example 32A tert-Butyl {1-(2-chlorophenyl)-2-[(2-methoxyethyl)-amino]-2-oxoethyl}carbamate A mixture of 250 mg (0.88 mmol) of <strong>[313490-25-4][(tert-butoxycarbonyl)amino](2-chlorophenyl)acetic acid</strong>, 177 mg (1.31 mmol) of HOBt, 252 mg (1.31 mmol) of EDC and 72 mg (0.96 mmol) of 2-methoxyethanamine in 6.3 ml of DMF was stirred at RT for 2 h. For purification, 1 ml of 1N hydrochloric acid was added and the entire reaction mixture was separated by preparative HPLC [Method 6]. The appropriate fraction was concentrated on a rotary evaporator and the residue was dried under high vacuum. This gave 269 mg (90% of theory) of the title compound. LC-MS [Method 5]: Rt=0.88 min; MS [ESIpos]: m/z=343 (M+H)+ 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=1.38 (s, 9H), 3.18-3.29 (m, 2H), 3.22 (s, 3H), 3.29-3.37 (m, 2H), 5.45 (d, 1H), 7.28-7.34 (m, 2H), 7.35-7.46 (m, 2H), 7.49 (d, 1H), 8.06 (br. t, 1H).

References: [1]Patent: US2013/231313,2013,A1 .Location in patent: Paragraph 0473; 0474; 0475; 0476.

6
[ 313490-25-4 ]
[ 6232-11-7 ]
C₂₂H₂₅ClN₂O₅ [ No CAS ]