[ CAS No. 51301-86-1 ] {[proInfo.proName]}

Name: 51301-86-1|2-((tert-Butoxycarbonyl)amino)-3-(4-chlorophenyl)propanoic acid|98%
Brand: Ambeed
SKU: A105710
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Quality Control of [ 51301-86-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 51301-86-1 ]

SDS Specification

Alternatived Products of [ 51301-86-1 ]

Product Details of [ 51301-86-1 ]

CAS No. :	51301-86-1	MDL No. :	MFCD02081080
Formula :	C₁₄H₁₈ClNO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	299.75	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 51301-86-1 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.43
Num. rotatable bonds :	7
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	76.35
TPSA :	75.63 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.4
Log Po/w (XLOGP3) :	3.69
Log Po/w (WLOGP) :	2.86
Log Po/w (MLOGP) :	2.49
Log Po/w (SILICOS-IT) :	2.3
Consensus Log Po/w :	2.75

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-3.78
Solubility :	0.0494 mg/ml ; 0.000165 mol/l
Class :	Soluble
Log S (Ali) :	-4.97
Solubility :	0.00322 mg/ml ; 0.0000108 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.78
Solubility :	0.0496 mg/ml ; 0.000166 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.74

Safety of [ 51301-86-1 ]

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

Application In Synthesis of [ 51301-86-1 ]

* 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.

Upstream synthesis route of [ 51301-86-1 ]
Downstream synthetic route of [ 51301-86-1 ]

[ 51301-86-1 ] Synthesis Path-Upstream 1~11

1
[ 159750-06-8 ]
[ 51301-86-1 ]

Reference： [1] Journal of Organic Chemistry, 1997, vol. 62, # 13, p. 4536 - 4538
[2] Journal of Organic Chemistry, 1994, vol. 59, # 9, p. 2304 - 2313

2
[ 24424-99-5 ]
[ 14173-39-8 ]
[ 51301-86-1 ]

Reference： [1] Patent: US6342629, 2002, B1, . Location in patent: Example 3
[2] Tetrahedron Letters, 1998, vol. 39, # 39, p. 7201 - 7204

3
[ 24424-99-5 ]
[ 7424-00-2 ]
[ 77-92-9 ]
[ 51301-86-1 ]

Reference： [1] Patent: EP1211249, 2002, A1,

4
[ 24424-99-5 ]
[ 51301-86-1 ]

Reference： [1] Journal of Organic Chemistry, 1997, vol. 62, # 13, p. 4536 - 4538
[2] Journal of Organic Chemistry, 1994, vol. 59, # 9, p. 2304 - 2313

5
[ 159750-02-4 ]
[ 51301-86-1 ]

Reference： [1] Journal of Organic Chemistry, 1997, vol. 62, # 13, p. 4536 - 4538
[2] Journal of Organic Chemistry, 1994, vol. 59, # 9, p. 2304 - 2313

6
[ 2019-34-3 ]
[ 51301-86-1 ]

Reference： [1] Journal of Organic Chemistry, 1994, vol. 59, # 9, p. 2304 - 2313

7
[ 1615-02-7 ]
[ 51301-86-1 ]

Reference： [1] Journal of Organic Chemistry, 1994, vol. 59, # 9, p. 2304 - 2313

8
[ 1027659-22-8 ]
[ 51301-86-1 ]

Reference： [1] Journal of Organic Chemistry, 1994, vol. 59, # 9, p. 2304 - 2313

9
[ 159750-01-3 ]
[ 51301-86-1 ]

Reference： [1] Journal of Organic Chemistry, 1994, vol. 59, # 9, p. 2304 - 2313

10
[ 1070-19-5 ]
[ 14173-39-8 ]
[ 51301-86-1 ]

Reference： [1] Acta Chimica Academiae Scientiarum Hungaricae, 1980, vol. 104, # 3, p. 227 - 233

11
[ 67-56-1 ]
[ 51301-86-1 ]
[ 14173-40-1 ]

Reference： [1] Journal of Peptide Science, 2012, vol. 18, # 6, p. 418 - 426

[ 51301-86-1 ] Synthesis Path-Downstream 1~38

1
[ 1070-19-5 ]
[ 14173-39-8 ]
[ 51301-86-1 ]

Reference： [1]Acta Chimica Academiae Scientiarum Hungaricae,1980,vol. 104,p. 227 - 233

2
[ 24424-99-5 ]
[ 14173-39-8 ]
[ 51301-86-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hydroxide; In water; acetone; at 0 - 20℃;	To a solution of j?-chloro-L-phenylalanine (18.0 g, 75 mmol) in acetone-water (150 mL : 150 mL) was added sodium hydroxide (6 g, 150 mmol) at 0 C followed by di-tert-buty dicarbonate (16.4 g, 75 mmol). The reaction mixture was stirred at room temperature overnight. Acetone was evaporated. Aqueous layer was acidified to pH 2 with 2 M HC1 and extracted with ethyl acetate. Organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was crystallized from hexane to obtain 18.0 g of product 19a as white solid (80% yield).ESI-MS m/z for Ci4Hi8ClN04found 299.8 / 301.8 (M+l)+ NMR (DMSO-de, 500 MHz) delta: 7.29(d, J = 8.3 Hz, 2H), 7.21 (d, J = 8.3 Hz, 2H), 7.02 (d, J = 7.3 Hz, 1H), 4.08-3.99 (m, 1H), 2.96 (dd, J = 4.3, 13.7Hz, 1H), 2.76 (dd, J = 10.5, 13.6 Hz, 1H).

Reference： [1]Patent: US6342629,2002,B1 .Location in patent: Example 3
[2]Patent: WO2017/37670,2017,A1 .Location in patent: Page/Page column 138; 139
[3]Tetrahedron Letters,1998,vol. 39,p. 7201 - 7204

3
[ 3978-80-1 ]
[ 61925-78-8 ]
[ 51301-86-1 ]
S-p-MeBzl-N^α-Boc-D-Pen Merrifield [ No CAS ]
Tyr-D-Cys-p-ClPhe-D-Pen-OH [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1535 - 1541

4
6-bromoisoatoic anhydride [ No CAS ]
[ 14173-39-8 ]
[ 51301-86-1 ]
D,L-N-(2-Amino-5-bromobenzoyl)-4-chlorophenylalanine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With hydrogenchloride; In 1,4-dioxane; pyridine;	A. D,L-N-(2-Amino-5-bromobenzoyl)-4-chlorophenylalanine D,L-4-chlorophenylalanine (prepared from N-Boc-D,L-4-chlorophenylalanine and 4N HCl in dioxane with dimethyl sulfide) and 6-bromoisoatoic anhydride (1.0 g, 4.15 mmol) were combined in pyridine (50 mL) and the mixture was refluxed for 4 h. The mixture was cooled, concentrated and the residue was partitioned between water (200 mL) and ethyl acetate (200 mL). The organic layer was washed with water (3*100 mL), brine (50 mL), dried (MgSO4) and concentrated to yield Compound A as a yellowish glass (450 mg, 27%), MS (M+H)+ 398.

Reference： [1]Patent: US6011029,2000,A

5
[ 24424-99-5 ]
[ 7424-00-2 ]
[ 77-92-9 ]
[ 51301-86-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; water;	Reference Example 6 (2S)-2-(tert-Butoxycarbonyl)amino-3-(4-chlorophenyl)propionic acid (Reference compound No. 6-1) Triethylamine (1.05 ml) is added to a suspension of p-chlorophenylalanine (1.00 g) in water (5 ml). Then, a solution of di-tert-butyl dicarbonate (1.20 g) in tetrahydrofuran (5 ml) is added to the mixture, and the whole is stirred for three hours. The reaction mixture is concentrated under reduced pressure, an aqueous citric acid solution is added to the resulting residue, and the whole is extracted with ethyl acetate. The extract is washed with water and saturated brine successively and dried over anhydrous magnesium sulfate. The extract is concentrated under reduced pressure to give the titled reference compound (1.47 g). mp 108.9-112.4C [alpha]D20+12.7 (c=1.0, methanol) IR(KBr, cm-1)3347,2990,2930,1713,1689,1522

Reference： [1]Patent: EP1211249,2002,A1

6
[ 51301-86-1 ]
[ 87571-88-8 ]
[ 1310688-22-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3163 - 3167

7
[ 67-56-1 ]
[ 51301-86-1 ]
[ 14173-40-1 ]

Reference： [1]Journal of Peptide Science,2012,vol. 18,p. 418 - 426

8
[ 51301-86-1 ]
[ 131019-87-9 ]
tert-butyl N-[(1S)-1-[(4-chlorophenyl)methyl]-2-[4-methyl-2-(methylamino)anilino]-2-oxo-ethyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at -20 - 20℃; for 15.0h;	To a solution of (2S)-2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoic acid (460 mg, 1.53 mmol) in DMF (15 ml), <strong>[131019-87-9]N2,4-dimethylbenzene-1,2-diamine</strong>1 (208 mg, 1.53 mmol) was added at 0 oC. Subsequently, HOAt (250 mg, 1.86 mmol) and WSCI.HCl (480 mg, 2.53 mmol) were added to the former solution at -20 oC and stirred for 15 h at ambient temperature. The reaction mixture was quenched with sat.NaHCO3 and extracted with EtOAc. The combined extracts were washed with H2O and brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 15a in 83 % yield. Rf=0.68 (n-Hexane/EtOAc=1/1). 1H NMR (600 MHz, CDCl3): delta 7.32 (d, J=8.2 Hz, 2H), 7.22 (d, J=8.2 Hz, 2H), 7.06 (s, 1H), 6.94 (d, J=7.8 Hz, 1H), 6.51 (d, J=7.56 Hz, 1H), 6.48 (s, 1H), 5.07 (brs, 1H), 4.35 (q, J=7.3 Hz, 1H), 3.66 (brs, 1H), 3.14-3.09 (m, 2H), 2.74 (s, 3H), 2.29 (s, 3H), 1.45 (s, 9H). HRMS (ESI/TOF) m/z: [M+H]+ Calcd for C22H29Cl1N3O3 418.18974 ; Found 418.19194.

Reference： [1]Bioorganic and Medicinal Chemistry,2019

9
C₃H₈NPol [ No CAS ]
[ 68858-20-8 ]
Fmoc-(R)-Arg(Pbf)-OH [ No CAS ]
[ 35661-40-6 ]
[ 51301-86-1 ]
[ 132388-59-1 ]
[ 102971-73-3 ]
[ 88050-17-3 ]
C₄₇H₆₉ClN₁₂O₁₁S [ No CAS ]