13122-90-2|Boc-Phe-Phe-OH| Ambeed

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Quality Control of [ 13122-90-2 ] Purity: 97% SDS Specification

COA

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Product Details of [ 13122-90-2 ]

CAS No. :	13122-90-2
Formula :	C₂₃H₂₈N₂O₅
M.W :	412.48
SMILES Code :	O=C(O)[C@@H](NC([C@@H](NC(OC(C)(C)C)=O)CC1=CC=CC=C1)=O)CC2=CC=CC=C2
MDL No. :	MFCD00190824
InChI Key :	NNOBHAOOLCEJBL-OALUTQOASA-N
Pubchem ID :	7019052

Safety of [ 13122-90-2 ]

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

Computational Chemistry of [ 13122-90-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	30
Num. arom. heavy atoms	12
Fraction Csp3	0.35
Num. rotatable bonds	12
Num. H-bond acceptors	5.0
Num. H-bond donors	3.0
Molar Refractivity	113.25
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	104.73 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.97
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	3.15
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.93
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.	2.55
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	3.1
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.74

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.89
Solubility	0.0536 mg/ml ; 0.00013 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.	-5.02
Solubility	0.00395 mg/ml ; 0.00000957 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	-6.06
Solubility	0.000362 mg/ml ; 0.000000877 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly 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	Yes
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.	-6.58 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	1.0
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<2.0
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)	3.74

Application In Synthesis of [ 13122-90-2 ]

* 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 [ 13122-90-2 ]

[ 13122-90-2 ] Synthesis Path-Downstream 1~35

1
[ 13122-90-2 ]
[ 100-39-0 ]
[ 16879-80-4 ]

References: [1]Journal of Organic Chemistry,1977,vol. 42,p. 1286 - 1290.

2
[ 6066-82-6 ]
[ 13122-90-2 ]
[ 189062-72-4 ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-carbodiimide; In 1,2-dimethoxyethane; at 0℃; for 2h;Inert atmosphere;	(BOC)FF-NHS (3): Compound 2 (0.5 g, 1.2 mmol) and N-Hydroxy succinimide (0.153 g, 1.3 mmol) were dissolved in 1,2-dimethoxy ethane (10 ml) and reaction mixture was cooled to 0 C under nitrogen atmosphere. A solution of DCC (0.274 g, 1.3 mmol) in 1,2-dimethoxy ethane (5 ml) was added into the reaction mixture dropwise and reaction mixture was stirred for 2 h at 0 C. After which the reaction mixture was kept in a freezer overnight. The reaction mixture was filtered and filtrate was concentrated under reduced pressure. Solid material was washed with diethyl ether and dried under high vaccum. Crude compound 3 (0.6 g, 1.1 mmol) was directly used for synthesis of compounds 4 and 6.
	With dicyclohexyl-carbodiimide; In dichloromethane; at -5℃;	General procedure: A round-bottom flask was charged with amino acid (2.5 mmol), NaHCO3 (5 mmol, or 7.5 mmol in the case of using TFA salt of amino acid) and THF-H2O (1:1,20 mL). A solution of succinimide-activated amino acid (2.75 mmol) in THF (15 mL) was added dropwise to the mixture, and the reaction was stirred at rt for 1-2 days. THF was removed on a rotary evaporator, the reaction mixture was acidified with 0.5 M HCl to pH 2, and the product was extracted with ethyl acetate (3 x 30 mL). The organic layers were washed with water and dried over anhydrous Na2SO4. After filtration and evaporation of the solvent, the product was purified by column chromatography on silica gel.

References: [1]European Journal of Medicinal Chemistry,1992,vol. 27,p. 179 - 186.
[2]Tetrahedron,2013,vol. 69,p. 2004 - 2009.
[3]Research on Chemical Intermediates,2017,vol. 43,p. 5305 - 5320.
[4]Journal of Organic Chemistry,2018,vol. 83,p. 14905 - 14922.

3
[ 24424-99-5 ]
[ 2577-40-4 ]
[ 13122-90-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20℃; for 3.5h;	A solution of (Boc) 20 (800 mg, 3.5 mmol) in 1,4-dioxane (5 ML) was added to a cold (0 C) solution OF DI-L-PHE-PHE (1 g, 3.20 mmol) in 1,4-dioxane (6 mL) and 1N NAOH (3.3 mL). The mixture was stirred at 0-5 C FOR 2 hours. Another portion of (BOC) 20 (100 mg) was added and the mixture was stirred for an additional 60 minutes at 0-5 C then at room temperature for 30 minutes. The mixture was then evaporated to dryness. The solid was taken in a mixture of water/EtOAc and pH was adjusted to 2 with 2N HCI. The aqueous layer was extracted 3 times with EtOAc. The combined organic layers were dried with brine and the solvent was evaporated. Some solid was insoluble in a mixture of EtOAc/CHC13 : it was removed by filtration. The desired N Boc-L-Phe-L-Phe 1 was obtained as a white foamy solid (913.7 mg, 2.215 mmol, 71% yield).

References: [1]Patent: WO2004/113275,2004,A2 .Location in patent: Page 158; 159.
[2]Journal of the American Chemical Society,2007,vol. 129,p. 2959 - 2966.
[3]Angewandte Chemie - International Edition,2008,vol. 47,p. 1758 - 1761.

4
[ 930275-52-8 ]
[ 13122-90-2 ]
(1-{1-[1-(furan-2-carbonyl)-2-methyl-propylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1102 - 1106.

5
(2S,3R)-2-amino-1-(furan-2-yl)-3-methylpentan-1-one [ No CAS ]
[ 13122-90-2 ]
(1-{1-[1-(furan-2-carbonyl)-2-methyl-butylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1102 - 1106.

6
[ 930275-53-9 ]
[ 13122-90-2 ]
(1-{1-[1-(furan-2-carbonyl)-3-methyl-butylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1102 - 1106.

7
[ 13122-90-2 ]
[ 2365-48-2 ]
[2-(2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-3-phenyl-propionylsulfanyl]-acetic acid methyl ester [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 1758 - 1761.
[2]Journal of the American Chemical Society,2007,vol. 129,p. 2959 - 2966.

8
[ 63-91-2 ]
[ 13122-90-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1102 - 1106.
[2]Soft Matter,2012,vol. 8,p. 5621 - 5628.
[3]Chemistry - An Asian Journal,2013,vol. 8,p. 113 - 120.
[4]Chemistry - An Asian Journal,2013,vol. 8,p. 113 - 120.
[5]Chemical Communications,2016,vol. 52,p. 5045 - 5048.

9
[ 2577-90-4 ]
[ 13122-90-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1102 - 1106.
[2]Organic Letters,2004,vol. 6,p. 3433 - 3436.
[3]Soft Matter,2012,vol. 8,p. 5621 - 5628.
[4]Chemistry - An Asian Journal,2013,vol. 8,p. 113 - 120.
[5]Patent: WO2016/181408,2016,A2 .
[6]Angewandte Chemie - International Edition,2017,vol. 56,p. 13288 - 13292.
Angew. Chem.,2017,vol. 129,p. 13473 - 13477,5.

10
[ 13122-90-2 ]
(S)-6-Amino-2-[(S)-2-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-3-phenyl-propionylamino]-hexanoic acid methyl ester [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 3433 - 3436.

11
[ 13122-90-2 ]
6-tert-butoxycarbonylamino-2-[2-(2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-3-phenyl-propionylamino]-hexanoic acid methyl ester [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 3433 - 3436.

12
[ 13122-90-2 ]
[ 786709-41-9 ]

References: [1]Organic Letters,2004,vol. 6,p. 3433 - 3436.

13
[ 3674-06-4 ]
[ 13122-90-2 ]

References: [1]Organic Letters,2004,vol. 6,p. 3433 - 3436.

14
[ 13122-90-2 ]
[ 763121-22-8 ]

References: [1]Collection of Czechoslovak Chemical Communications,2004,vol. 69,p. 776 - 796.

15
[ 13122-90-2 ]
[ 763121-24-0 ]

References: [1]Collection of Czechoslovak Chemical Communications,2004,vol. 69,p. 776 - 796.

16
[ 13122-90-2 ]
(S)-2-((S)-2-Amino-3-phenyl-propionylamino)-3-phenyl-propionic acid 2-oxo-2-phenyl-ethyl ester; hydrochloride [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,2004,vol. 69,p. 776 - 796.

17
[ 13734-34-4 ]
amino polystyrene [ No CAS ]
[ 13122-90-2 ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 6902 - 6910.

18
[ 17790-88-4 ]
[ 13122-90-2 ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 6902 - 6910.

19
[ 13122-90-2 ]
(S)-2-[(S)-2-((S)-2-Amino-3-phenyl-propionylamino)-3-phenyl-propionylamino]-3-phenyl-propionic acid 10-bromo-decyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,1998,vol. 120,p. 12192 - 12199.

20
[ 13122-90-2 ]
(S)-3-Phenyl-2-[(S)-3-phenyl-2-((S)-3-phenyl-2-tridecanoylamino-propionylamino)-propionylamino]-propionic acid 10-bromo-decyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,1998,vol. 120,p. 12192 - 12199.

21
[ 13122-90-2 ]
Trimethyl-(10-{(S)-3-phenyl-2-[(S)-3-phenyl-2-((S)-3-phenyl-2-tridecanoylamino-propionylamino)-propionylamino]-propionyloxy}-decyl)-ammonium; bromide [ No CAS ]

References: [1]Journal of the American Chemical Society,1998,vol. 120,p. 12192 - 12199.

22
[ 13122-90-2 ]
(R)-4-{(3R,5R,8R,9S,10S,13R,14S,17R)-3-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-3-phenyl-propionylamino]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid [ No CAS ]