261165-05-3|(1S,3R)-3-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid| Ambeed

Structure of Boc-D-AcPAC
CAS No.: 261165-05-3

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Synonyms: BOC-(1S,3R)-3-Aminocyclopentanecarboxylic acid; (1S,3R)-3-[(tert-Butoxycarbonyl)amino]cyclopentanecarboxylic acid

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Quality Control of [ 261165-05-3 ] Purity: 97% SDS Specification

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Product Details of [ 261165-05-3 ]

CAS No. :	261165-05-3
Formula :	C₁₁H₁₉NO₄
M.W :	229.27
SMILES Code :	O=C([C@@H]1C[C@H](NC(OC(C)(C)C)=O)CC1)O
Synonyms :	BOC-(1S,3R)-3-Aminocyclopentanecarboxylic acid; (1S,3R)-3-[(tert-Butoxycarbonyl)amino]cyclopentanecarboxylic acid
MDL No. :	MFCD01320857
InChI Key :	RNJQBGXOSAQQDG-JGVFFNPUSA-N
Pubchem ID :	1512529

Safety of [ 261165-05-3 ]

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

Computational Chemistry of [ 261165-05-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	0
Fraction Csp3	0.82
Num. rotatable bonds	5
Num. H-bond acceptors	4.0
Num. H-bond donors	2.0
Molar Refractivity	59.16
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.	2.08
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	1.37
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.76
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.	1.03
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	0.55
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.36

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.79
Solubility	3.68 mg/ml ; 0.016 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.	-2.56
Solubility	0.63 mg/ml ; 0.00275 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	-1.14
Solubility	16.6 mg/ml ; 0.0724 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.	-6.73 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)	2.98

Application In Synthesis of [ 261165-05-3 ]

* 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 [ 261165-05-3 ]

[ 261165-05-3 ] Synthesis Path-Downstream 1~35

1
[ 543-27-1 ]
[ 261165-05-3 ]
C₁₆H₂₇NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In diethyl ether; at -20℃; for 0.583333h;	Isobutyl chloroformate (1.21 g, 8.90 mmol) was added to a well-stirred solution of Intermediate 7 (2.09 g, 8.72 mmol) and triethylamine (890 mg, 8.72 mmol) in dry ether (15 ml) at - 20 0C over 5 min under a nitrogen atmosphere. The reaction mixture was stirred for another 30 min at the same temperature and then filtered to remove the precipitated triethylamine hydrochloride. To the filtrate containing the mixed anhydride was slowly added a solution of diazomethane in diethyl ether until the yellow colour persisted (ca. 20 ml). The reaction mixture was gradually allowed to warm to room temperature and left overnight at this temperature. Excess diazomethane was quenched with a few drops of glacial acetic acid and then with 10 % citric acid solution. The organic layer was separated and the aqueous layer was extracted with ether (2 x 100 ml). The combined organic extracts were washed with saturated NaHCO3 solution, brine and dried (Na2SO4). The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography (30 % ethyl acetate in petroleum ether) to afford 1.12 g of the desired compound as a pale yellow solid; IR (KBr) 3355, 3079, 2136, 1685, 1614, 1530 cm"1; 1H NMR (CDCl3) 1.44 (s, 9H), 1.60-1.93 (m, 5H), 2.04-2.14 (m, IH), 2.82 (brs, IH), 4.06 (brs, IH), 5.28 (brs, IH).

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3103 - 3107.
[2]Patent: WO2006/40625,2006,A1 .Location in patent: Page/Page column 54.

2
N-(6-aminobenzothiazol-2-yl)cyclopentanecarboxamide [ No CAS ]
[ 261165-05-3 ]
{(1R,3S)-3-[2-(Cyclopentanecarbonyl-amino)-benzothiazol-6-ylcarbamoyl]-cyclopentyl}-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2509 - 2522.

3
cis-3-aminocyclopentanecarboxylic acid hydrochloride [ No CAS ]
[ 24424-99-5 ]
[ 161660-94-2 ]
[ 261165-05-3 ]

References: [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 5710 - 5713.

4
[ 580-22-3 ]
[ 261165-05-3 ]
(1S,3R)-[3-(quinolin-2-ylcarbamoyl)-cyclopentyl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With EDAC; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;	Example 192A (1S,3R)-[3-(quinolin-2-ylcarbamoyl)-cyclopentyl]-carbamic acid tert-butyl ester To a solution of Example 191A (91.6 mg, 0.4 mmol) in DMF (4 mL) was added 2-aminoquinoline (64 mg, 0.44 mmol), EDAC (93 mg, 0.48 mmol), HOBT (82 mg, 0.6 mmol), and diisopropylethylamine (0.35 mL, 2 mmol). The mixture was stirred at room temperature overnight, diluted with ethyl acetate, washed with water (2 times) and brine. The organic layer was dried (sodium sulfate), filtered, concentrated under reduced pressure and purified by flash chromatography with 3% methanol/dichloromethane to provide the titled compound. MS (ESI) m/z 356 (M+H)+.

References: [1]Patent: US2005/215784,2005,A1 .

5
[ 261165-05-3 ]
[ 554451-12-6 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; methanol; hexane;	Example 195A <strong>[261165-05-3](1S,3R)-3-tert-butoxycarbonylamino-cyclopentanecarboxylic acid</strong> methyl ester To a cold solution (0 C.) of Example 191A (458 mg, 2 mmol)in THF (2 mL)/MeOH (2 mL) was added TMSCHN2 (2 mL, 2N in hexane). The mixture was stirred at room temperature for 2 hours, concentrated under reduced pressure and purified by flash chromatography with 30% acetone/hexane to provide the titled compound. MS (ESI) m/z 244 (M+H)+.

References: [1]Patent: US2005/215784,2005,A1 .

6
[ 24647-29-8 ]
[ 261165-05-3 ]

References: [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 5710 - 5713.

7
[ 49805-30-3 ]
[ 261165-05-3 ]

References: [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 5710 - 5713.

8
[ 261165-05-3 ]
[ 878395-68-7 ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2509 - 2522.

9
[ 261165-05-3 ]
(1S,3R)-3-[(Naphthalen-2-ylmethyl)-amino]-cyclopentanecarboxylic acid [2-(cyclopentanecarbonyl-amino)-benzothiazol-6-yl]-amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2509 - 2522.

10
[ 261165-05-3 ]
[ 551964-49-9 ]