[ CAS No. 225517-81-7 ] {[proInfo.proName]}

Name: 225517-81-7|Methyl (S)-4-N-Cbz-piperazine-2-carboxylate|97%
Brand: Ambeed
SKU: A473813
Rating: 91 (28 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 225517-81-7 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 225517-81-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 225517-81-7 ]

SDS Specification

Alternatived Products of [ 225517-81-7 ]

Product Details of [ 225517-81-7 ]

CAS No. :	225517-81-7	MDL No. :	MFCD04115338
Formula :	C₁₄H₁₈N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FYKXWBBQYZXPFB-LBPRGKRZSA-N
M.W :	278.30	Pubchem ID :	7023277
Synonyms :

Calculated chemistry of [ 225517-81-7 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.43
Num. rotatable bonds :	6
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	79.43
TPSA :	67.87 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.34 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.7
Log Po/w (XLOGP3) :	0.92
Log Po/w (WLOGP) :	-0.14
Log Po/w (MLOGP) :	0.76
Log Po/w (SILICOS-IT) :	0.86
Consensus Log Po/w :	1.02

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.97
Solubility :	2.97 mg/ml ; 0.0107 mol/l
Class :	Very soluble
Log S (Ali) :	-1.93
Solubility :	3.26 mg/ml ; 0.0117 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.83
Solubility :	0.41 mg/ml ; 0.00147 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.99

Safety of [ 225517-81-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 225517-81-7 ]

* 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.

Upstream synthesis route of [ 225517-81-7 ]
Downstream synthetic route of [ 225517-81-7 ]

[ 225517-81-7 ] Synthesis Path-Upstream 1~1

1
[ 129799-11-7 ]
[ 225517-81-7 ]
[ 1394957-81-3 ]
[ 405175-79-3 ]

Reference： [1] Chemical Communications, 2012, vol. 48, # 71, p. 8892 - 8894

[ 225517-81-7 ] Synthesis Path-Downstream 1~11

1
3(R)-amino-3-(4-hydroxphenyl)propionic acid, methyl ester, acetic acid salt [ No CAS ]
3,5-dichlorobenzenenesulfonyl chloride [ No CAS ]
[ 225517-81-7 ]
(1-(3,5-dichlorobenzenesulfonyl)-4-(benzyloxycarbonyl))piperazine-2(S)-carboxylic Acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step B. (1-(3,5-dichlorobenzenesulfonyl)-4-(benzyloxycarbonyl))piperazine-2(S)-carboxylic Acid, Methyl Ester The title compound was prepared by reacting <strong>[225517-81-7]2(S)-4-(benzyloxycarbonyl)piperazine-2-carboxylic acid, methyl ester</strong> with 3,5-dichlorobenzenenesulfonyl chloride as taught in Example 28, Step D. 400 MHz 1H NMR (CDCl3): 2.9-3.0 (m, 1H), 3.15-3.25 (m, 1H), 3.3-3.4 (m, 2H), 3.5-3.6 (m, 1H), 4.1-4.3 (bd, 1H), 5.0 (d, 1H, J=12 Hz), 7.2-7.35 (m, 5H), 7.53 (t, 1H), J=2 Hz), 7.59 (t, 2H; J=2 Hz).

Reference： [1]Patent: US6645939,2003,B1

2
[ 954382-59-3 ]
[ 225517-81-7 ]
C₃₃H₃₄N₄O₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4833 - 4837

3
[ 954382-71-9 ]
[ 225517-81-7 ]
C₃₃H₃₃FN₄O₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4833 - 4837

4
[ 129799-11-7 ]
C₁₅H₂₀O₂ [ No CAS ]
[ 225517-81-7 ]
[ 1394957-81-3 ]
1-benzyl 3-methyl (3S)-4-(3-mesitylpropanoyl)piperazine-1,3-dicarboxylate [ No CAS ]
[ 405175-79-3 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 8892 - 8894

Yield	Reaction Conditions	Operation in experiment
55%; 44%	With 2-(2,4,6-trimethyl-phenyl)-2,5,6,7-tetrahydro-pyrrolo[2,1-c] [1,2,4]triazol-4-ylium perchlorate; (4aR,9aS)-6-bromo-4-hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one; potassium carbonate; In Isopropyl acetate; at 23℃; for 24.0h;	General procedure: Example 19: Improved General Procedure for the KineticResolution of Secondary AminesThe hydroxamic acid co-catalyst of example 18 (7.1 mg, 25 pmol, 0.05 equiv) , triazolium salt (16.4 mg, 50 muiotaetaomicron, 0.10 equiv), ' -hydroxyenone (81.4 mg, 0.35 mmol, 0.70 equiv), K2C03 (13.8 mg, 0.1 mmol, 0.20 equiv) and the respective amine (0.50 mmol, 1.00 equiv) were dissolved in iPrOAc (2.5 ml, 0.20 M) and the reaction mixture was stirred at 23 C for 24 hours.EtOAc (25 ml) was added, the mixture was filtered through Celite and concentrated in vacuo. The crude products were purified by column chromatography. Example 20: Kinetic Resolution of Racemic 3-Methylpip zin-2-oneRacemic 3-methylpiperazin-2-one (57.1 mg, 0.50 mmol) was resolved according to the improved general procedure (Example 19) .Recovered amine: 24 mg (42%, er = 90:10); acylated product: 80 mg (56%, er = 79:21).Calculated conversion: 58%; s = 9.Recovered amine: (3R) -3-methylpiperazin-2-oneThe amine was protected with benzyl chloroformate to determine the er:[a] 28D (c = 0.2, CHC13) : +/- 0.0;SFC : column: Daicel Chiralpak ASH (4.6 chi 250 mm) ; gradient: 5% iPrOH in C02 to 50% iPrOH in C02 over 10 min; flow: 3.0 ml/min; detection: 254 nm. Retention time: tR = 6.8 min (major) and 7.3 min (minor) .Amide product: (3S) -4- (3-Mesitylpropanoyl) -3-methylpipera- zin-2-one Me O Me [a] D (c = 4.0, CHC13) : +59.6; at room temperature the ratio of rotamers was 50:50 as determined by XH NMR;13C NMR (100 MHz, CDC13) : delta [ppm] = 171.9, 170.8, 170.5, 170.3, 136.0, 135.9, 135.7, 134.2, 134.1, 129.0, 53.9, 51.2, 41.3, 41.2, 38.9, 34.4, 32.4, 31.8, 24.7, 24.6, 20.7, 19.7, 17.8, 16.4;XH NMR (400 MHz, CDCI3) : delta [ppm] = 6.83 (s, 2 H) , 5.05 (q, J = 7.1 Hz, 0.5 H), 4.70 (dd, J = 13.6, 2.4 Hz, 0.5 H) , 4.28 (q, J = 7.1 Hz, 0.5 H), 3.69 (br d, J = 12.6 Hz, 0.5 H) , 3.46-3.21 (m, 2.5 H) , 3.05-2.90 (m, 2.5 H) , 2.58-2.32 (m, 2 H), 2.28 (s, 6 H) , 2.23 (s, 3 H) ; 1.44 (t, J = 6.5 Hz, 3 H) ;HRMS (ESI): calculated for [C17H25N2O2] + : m/z = 289.1911, found: m/z = 289.1914;IR (v /cm-1, neat) : 3244, 2998, 2944, 2921, 1668, 1648, 1457, 1427, 1332, 1208, 1091, 1062;SFC: column: Daicel Chiralpak ODH (4.6 * 250 mm); gradient: 5% iPrOH in C02 to 50% iPrOH in C02 over 10 min; flow: 3.0 ml/min; detection: 254 nm. Retention time: tR = 7.8 min (minor) and 9.4 min (major).

6
[ 225517-81-7 ]
[ 100564-78-1 ]
C₂₉H₃₇N₃O₇ [ No CAS ]