718611-17-7|(S)-Boc-3-Amino-3-phenylpropan-1-ol| Ambeed

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Quality Control of [ 718611-17-7 ] Purity: 97% SDS Specification

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Product Details of [ 718611-17-7 ]

CAS No. :	718611-17-7
Formula :	C₁₄H₂₁NO₃
M.W :	251.32
SMILES Code :	OCC[C@H](NC(OC(C)(C)C)=O)C1=CC=CC=C1
MDL No. :	MFCD09025325
InChI Key :	SMEMODSNLZWKBF-LBPRGKRZSA-N
Pubchem ID :	7172194

Safety of [ 718611-17-7 ]

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

Computational Chemistry of [ 718611-17-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	18
Num. arom. heavy atoms	6
Fraction Csp3	0.5
Num. rotatable bonds	7
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	70.73
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	58.56 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.69
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	2.13
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.31
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.	2.07
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	2.06
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.25

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.52
Solubility	0.751 mg/ml ; 0.00299 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.	-2.99
Solubility	0.256 mg/ml ; 0.00102 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-3.64
Solubility	0.058 mg/ml ; 0.000231 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.	-6.32 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.	0.55

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 [ 718611-17-7 ]

* 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 [ 718611-17-7 ]

[ 718611-17-7 ] Synthesis Path-Downstream 1~35

1
[ 956101-46-5 ]
[ 718611-17-7 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 7094 - 7098.
[2]Tetrahedron Letters,1994,vol. 35,p. 1589 - 1592.

2
[ 718611-17-7 ]
[ 103365-47-5 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 7094 - 7098.
[2]Tetrahedron Letters,1994,vol. 35,p. 1589 - 1592.

3
[ 103365-47-5 ]
[ 718611-17-7 ]

Yield	Reaction Conditions	Operation in experiment
0.39 g	With borane-THF; In tetrahydrofuran; at 0℃; for 2h;Inert atmosphere;	will(S)-3-tert-butoxycarbonylamino-3-phenylalanine(0.40g, 1.5mmol)Dissolved in 5 mL THF,Nitrogen protection, at 0 C,Slowly add BH3THF (3 mL, 1 M/mL).Then continue the reaction for 2 hours.Adding an appropriate amount of acetone consumes excess BH3.Then add saturated sodium bicarbonate solution,The aqueous phase is extracted three times with ethyl acetate and the organic layers are combined.After washing the organic layer with saturated sodium chloride solution,After drying over anhydrous magnesium sulfate,Evaporated to get(S)-tert-Butyl-N-(3-hydroxy-1-phenylpropyl)carbamate0.39g (104%).
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 1h;	Method F (S) 3-PHENYL-3- (TERT-BUTOXYCARBONYLAMINO) propionaldehyde Lithium aluminium hydride (19 ml of 1M solution in THF) was added to a solution of (S) 3-phenyl-3- (tert-butoxycarbonylamino) propionic acid (5. 01G) in THF (50ML) at 0C. The reaction mixture was stirred for 1 hour and ethyl acetate (20ML) WAS added followed by water (0. 5ML), 6M sodium hydroxide (0. 5ml) and water (5ML). The mixture was filtered through CELITE and evaporated to dryness to give (S) 3-phenyl-3-(tert-butoxycarbonylamino)propanol, yield 2.89g. This material was dissolved in dichloromethane (40ML) and Dess Martin periodinane (2.12g) was added. The reaction mixture was stirred for 1 hour then washed with 2M sodium hydroxide (2X20ML) and brine (LOML) and dried. The dichloromethane solution was concentrated to a volume of about 20ML and used directly in the next stage.
	With sodium tetrahydroborate; In tetrahydrofuran; at 0℃; for 1h;	(S) 3-PHENYL-3-TERT-BUTOXYCARBONYLAMINO) propionaldehyde Lithium aluminium hydride (19 ml of 1M solution in THF) was added to a solution of (S) 3-PHENYL-3-(TERT-BUTOXYCARBONYLAMINO) propionic acid (5. 01G) in THF (50ml) at 0C. The reaction mixture was stirred for 1 hour and ethyl acetate (20ML) was added followed by water (0. 5ML), 6M sodium hydroxide (0. 5ML) and water (5ML). The mixture was filtered through Celite and evaporated to dryness to give (S) 3-PHENYL-3- (TERT-BUTOXYCARBONYLAMINO) propanol, yield 2.89g. This material was dissolved in dichloromethane (40ML) and Dess Martin periodinane (2.12g) was added. The reaction mixture was stirred for 1 hour then washed with 2M sodium hydroxide (2X20ML) and brine (10ML) and dried. The dichloromethane solution was concentrated to a volume of about 20ML and used directly in the next stage.

References: [1]Chirality,2010,vol. 22,p. 299 - 307.
[2]Heterocycles,1997,vol. 45,p. 1883 - 1889.
[3]European Journal of Organic Chemistry,2018,vol. 2018,p. 1821 - 1832.
[4]Patent: CN107879963,2018,A .Location in patent: Paragraph 0501-0502.
[5]Patent: WO2005/9959,2005,A1 .Location in patent: Page/Page column 51-52.
[6]Patent: WO2004/56773,2004,A1 .Location in patent: Page 92 - 93.

4
[ 718611-17-7 ]
[ 82769-76-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrogenchloride; In 1,4-dioxane; water;	In a 100 mL round bottom flask, 6 mmol / 1.51 g of the product of Example 4 was added.Add 30 mL of 1,4-dioxane,After thoroughly stirring and dissolving, 20 mL of a HCl (4M) aqueous solution was dropped into the flask,The solution was pale yellow,After the reaction of the raw materials is monitored by TLC,Extract once with 20 mL of ethyl acetate, take the aqueous phase, dropwise add NaOH (4M) aqueous solution in an ice bath,After adjusting the pH to 13, extract 3 times with 20 mL of dichloromethane.Take the organic phase, wash with saturated brine, and dry over anhydrous sodium sulfate.Preparation by flash liquid chromatography (methanol: dichloromethane = 1: 1-5: 1)Purified to obtain 0.87 g of colorless oily liquid compound 6,The yield was 96%.
0.016 g	With trifluoroacetic acid; In dichloromethane; at 0 - 20℃; for 2h;	To a solution of (XII) (0.030 g, 0.12 mmol) in DCM (2 mL) was added TFA (0.3 mL) drop wise at 0 C. It was kept at 0 C for half an hour and then allowed to come to room temperature and stirred for further 1.5 h. After completion (TLC), the reaction mixture was concentrated in vacuo to remove DCM and TFA. The residue was then dissolved in methanol (3 mL) and Et3N (0.016 mL, 0.12 mmol) was added and the resultant solution was passed through a short column of silica gel with methanol as an eluent. The methanol fractions were concentrated in vacuo to furnish 14 as a white hygroscopic solid (0.016 g, 89 nmax)

References: [1]Patent: CN110845369,2020,A .Location in patent: Paragraph 0102-0105.
[2]Tetrahedron,2009,vol. 65,p. 2605 - 2609.
[3]Heterocycles,1997,vol. 45,p. 1883 - 1889.
[4]Tetrahedron Asymmetry,2007,vol. 18,p. 2099 - 2103.
[5]Patent: EP2749553,2014,A1 .Location in patent: Paragraph 0102; 0103.

5
[ 496929-87-4 ]
[ 718611-17-7 ]
{3-[3-(2,6-difluoro-benzyl)-5-(2-fluoro-3-methoxy-phenyl)-2,4,6-trioxo-[1,3,5]triazinan-1-yl]-1-phenyl-propyl}-carbamic acid <i>tert</i>-butyl ester [ No CAS ]