132622-98-1|(2R,4R)-1-Boc-4-Aminopyrrolidine-2-carboxylic acid| Ambeed

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Quality Control of [ 132622-98-1 ] Purity: 95% SDS Specification

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Product Details of [ 132622-98-1 ]

CAS No. :	132622-98-1
Formula :	C₁₀H₁₈N₂O₄
M.W :	230.26
SMILES Code :	O=C([C@@H]1N(C(OC(C)(C)C)=O)C[C@H](N)C1)O
MDL No. :	MFCD08704542

Safety of [ 132622-98-1 ]

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

Computational Chemistry of [ 132622-98-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	0
Fraction Csp3	0.8
Num. rotatable bonds	4
Num. H-bond acceptors	5.0
Num. H-bond donors	2.0
Molar Refractivity	61.07
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	92.86 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.68
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	-2.28
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.03
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.	-0.07
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	-0.88
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.3

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	0.43
Solubility	624.0 mg/ml ; 2.71 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Highly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	0.86
Solubility	1690.0 mg/ml ; 7.32 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	0.21
Solubility	376.0 mg/ml ; 1.63 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.	-9.32 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	1.0
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<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)	3.1

Application In Synthesis of [ 132622-98-1 ]

* 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 [ 132622-98-1 ]

[ 132622-98-1 ] Synthesis Path-Downstream 1~19

1
[ 132622-98-1 ]
[ 2651-15-2 ]
[ 132622-99-2 ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 3009 - 3016.

2
[ 132622-97-0 ]
[ 132622-98-1 ]

Yield	Reaction Conditions	Operation in experiment
3 g	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 24.0h;	To a solution of (2 ?,4 ?)-2-benzyl 1-tert-butyl 4-azidopyrrolidine- l, 2- dicarboxylate (4.49 g, 12.9 mmol) in methanol (30 mL) was added Palladium on carbon (10%, 449 mg). The reaction vessel was evacuated by aspirator and thoroughly purged with hydrogen (three times), and the resulting heterogeneous mixture was stirred under a hydrogen balloon for 24 h at room temperature. The mixture was filtered through a pad of Celite and the pad was washed with methanol. The filtrate was concentrated in vacuo to give (27?,47?)-4-amino-l-(tert- butoxycarbonyl)pyrrolidine-2-carboxylic acid (3 g) which was used in the next step without purification. MS (ESI) m/z 175.1 [M+H-56]+.

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 3009 - 3016.
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 1771 - 1782.
[3]Patent: WO2019/28362,2019,A1 .Location in patent: Paragraph 00319; 00320; 00324; 00326.

3
[ 24424-99-5 ]
[ 132622-98-1 ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 3009 - 3016.

4
[ 132622-93-6 ]
[ 132622-98-1 ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 3009 - 3016.

5
[ 132622-89-0 ]
[ 132622-98-1 ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 3009 - 3016.

6
[ 132622-92-5 ]
[ 132622-98-1 ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 3009 - 3016.

Yield	Reaction Conditions	Operation in experiment
83%		EXAMPLE 39 STR38 (4R)-1-(tert-Butoxycarbonyl)-4-amino-D-proline (40). The azido benzyl ester (2.65 g, 7.65 mmol) was hydrogenated as for the preparation of 6. This gave 1.47 g (83% yield) of 40, m.p.=263-264 C. (decomp., darkening starting at 222 C.), after crystallization form water/EtOH. 1 H NMR (D2 O) delta1.42/1.46 (m, 9H), 2.11 (m, 1H), 2.68 (m, 1H), 3.70 (m, 2H), 4.00 (m, 2H), 4.18 (dd, J=9.0/3.9 Hz, 1H). Anal. (C10 H18 N2 O4.H2 O).

8
[ 132622-98-1 ]
(4S)-1-(tert-Butoxycarbonyl)-4-([(p-toluenesulfonyliminoaminomethyl)amino]methyl)-D-proline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%		EXAMPLE 40 STR39 (4R)-1-(tert-Butoxycarbonyl)-4-([(p-toluenesulfonyliminoaminomethyl)amino]methyl)-D-proline (41). Amino acid 40 (1.40 g, 5.74 mmol) was converted to 41 as for 13. The residue was recrystallized from EtOAc/Et2 O/hexane to give 1.87 g of 25 (59% yield), m.p.=132-133 C. 1 H NMR (d6 DMSO) delta1.33/1.38 (2s, 9H), 1.74 (m, 1H), 2.34 (s, 3H), 2.97 (m, 1H), 3.33 (m, 1H), 3.63 (m, 1H), 4.08 (m, 2H), 6.65 (bs, 2H), 6.93 (bs, 1H), 7.27 (d, J=8 Hz, 2H), 7.64 (d, J=8 Hz, 2H).

References: [1]Patent: US5120859,1992,A .

9
[ 132622-98-1 ]
Glycyl-[(4R)-4-([(iminoaminomethyl)amino]methyl)-D-prolyl]-glycyl-L-aspartyl-L-valine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 52 STR50 Glycyl-[(4R)-4-[(iminoaminomethyl)amino]methyl)-D-prolyl]-glycyl-L-aspartyl-L-valine. The title compound was obtained starting with the acid from Example 40 and the tripeptide resin of Example 42. The N-terminal glycine residue was coupled as in Example 42. Cleavage of the peptide from the resin and cleavage of the protective groups, and purification also as described in Example 42 afforded the desired title compound. FAB mass spectrum: calc.: 500; obs.: 501 (M+1). RP-HPLC retention time: 11 min.

References: [1]Patent: US5120859,1992,A .

10
[ 82911-69-1 ]
[ 132622-98-1 ]
[ 1018332-24-5 ]

Yield	Reaction Conditions	Operation in experiment
4 g	With sodium hydrogencarbonate; In tetrahydrofuran; water; at 0 - 20℃; for 2.0h;Inert atmosphere;	To a solution of (27?,47?)-4-amino- l-(tert- butoxycarbonyl)pyrrolidine-2-carboxylic acid (3 g, crude, 12.9 mmol) in Tetrahydrofuran (30 mL), 10% aqueous sodium bicarbonate solution (40 mL) was added. The solution was pre- cooled to 0 C, N-(9-Fluorenylmethoxycarbonyloxy)succinimide (4.37 g, 13 mmol) dissolved in tetrahydrofuran (20 mL) was then added. The reaction mixture was stirred for 2 h at room temperature and concentrated in vacuo to leave a residue which was dissolved in ethyl acetate (100 mL) and treated with saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate (3 xlOO mL) and the organic layers were collected, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a crude residue, which was purified by silica gel flash chromatography (ethyl acetate : methanol = 70 : 30) to afford (2R,4R)- 4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-l-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (4 g) as a white solid. 1H NMR (400Hz, CDC13) delta 7.73-7.7 l(m, 2 H), 7.58-7.48 (m, 2 H), 7.37-7.33 (m, 2 H), 7.29-7.26 (m, 2 H), 4.29-4.16 (m, 5 H), 3.69-3.44 (m, 2 H), 2.45 (s, 1 H), 2.31-2.14 (m, 2 H), 1.43 (s, 9 H).

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 1771 - 1782.
[2]Patent: WO2019/28362,2019,A1 .Location in patent: Paragraph 00319; 00320; 00324; 00327.

11
[ 147266-92-0 ]
[ 132622-98-1 ]