Home Cart 0 Sign in  

[ CAS No. 57292-44-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 57292-44-1
Chemical Structure| 57292-44-1
Structure of 57292-44-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 57292-44-1 ]

Related Doc. of [ 57292-44-1 ]

Alternatived Products of [ 57292-44-1 ]

Product Details of [ 57292-44-1 ]

CAS No. :57292-44-1 MDL No. :MFCD00076978
Formula : C14H18ClNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :BETBOAZCLSJOBQ-LLVKDONJSA-N
M.W : 299.75 Pubchem ID :7018791
Synonyms :

Calculated chemistry of [ 57292-44-1 ]

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 Ų

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) : 2.31
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 : 2.73

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 [ 57292-44-1 ]

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 [ 57292-44-1 ]

* 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 [ 57292-44-1 ]
  • Downstream synthetic route of [ 57292-44-1 ]

[ 57292-44-1 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 57292-44-1 ]
  • [ 14091-08-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 22, p. 3742 - 3755
  • 2
  • [ 14091-08-8 ]
  • [ 57292-44-1 ]
YieldReaction ConditionsOperation in experiment
87.3% With triethylamine In water; acetone at 20℃; for 44 h; The D-4-chlorophenylalanine crude product (22.0 mg, 0.110 mmol) was dissolved in water (2 mL) and acetone (1.0 mL). To the solution, a solution of (Boc)2O (40.4 mg, 0.185 mmol) in acetone (0.5 mL) and a solution of triethylamine (18.8 mg, 0.186 mmol) in acetone (0.5 mL) were added. The mixture was stirred at room temperature for 44 hours. The reaction mixture was concentrated until the volume was reduced to 2 mL or less, and then toluene (5 mL) was added thereto. To this, 4 N hydrochloric acid was added under stirring until the pH of the aqueous layer was reduced to 2 to 3. The organic layer was separated and washed with saturated brine (5 mL, twice). The organic layer was dried over magnesium sulfate, and then the solvent was removed by evaporation to give Boc-D-4-chlorophenylalanine (28.7 mg, 87.3percent, 98.6percent ee) as a white solid. (0304) HPLC analysis was conducted on the obtained compound under the following conditions. The results are shown in Table 5 and FIG. 5. <HPLC Conditions: Boc-D-4-Cl-Phe Chiral Analysis Conditions> Column: CHIRALPAK AD-RH (5 μm, 150×4.6 mm i.d.) Eluent: A:B=35:65 (0305) A=0.1percent phosphoric acid aqueous solution (0306) B=0.1percent solution of phosphoric acid in acetonitrile Flow rate: 1.0 mL/min Temperature: 35° C. Detector: UV 254 nm (0307) [table-us-00005-en] Retention time in HPLC (min) Isomer of Objective Excess ratio objective substance substance (isomer of objective Boc-L-4- Boc-D-4- substance:objective chlorophenylalanine chlorophenylalanine substance) 11.08 14.16 98.6percent ee (0.7:99.3)
Reference: [1] Patent: US2016/102045, 2016, A1, . Location in patent: Paragraph 0300-0307
  • 3
  • [ 24424-99-5 ]
  • [ 14091-08-8 ]
  • [ 57292-44-1 ]
YieldReaction ConditionsOperation in experiment
87.3% With triethylamine In water; acetone at 20℃; for 44 h; D-4- chlorophenylalanine crude product (22.0 mg, 0.110 mmol) was dissolved in water (2 mL) and acetone (1.0 mL), (Boc) 2O(40.4 mg, 0.185 mmol) acetone (0.5 mL) of solution of triethylamine (18.8 mg, 0.186 mmol) was stirred 44 hours at room temperature was added acetone (0.5 mL) solution of.After concentrated to the reaction mixture below 2 mL, it was added 4N hydrochloric acid under stirring by addition of toluene (5 mL) until the pH of the aqueous layer is 2-3.The organic layer prep to saturated brine (5 mL, 2 times) after drying washing and with magnesium sulfate, and the solvent was distilled off Boc-D-4- chloro-phenylalanine (28.7 mg, 87.3percent, 98.6 percent ee)as a white solid.
Reference: [1] Patent: KR2015/133268, 2015, A, . Location in patent: Paragraph 0484; 0486; 0488; 0499
  • 4
  • [ 14091-08-8 ]
  • [ 57292-44-1 ]
YieldReaction ConditionsOperation in experiment
90% With triethylamine In water; acetone at 25℃; for 14 h; General procedure: L-Phenylalanine (1.0 g, 6.05 mmol) and sodium carbonate (0.71 g, 6.70 mmol) in water (10 mL) was reacted with a solution of 2 (1.89 g, 6.36 mmol) in acetone (10 mL). The reaction mixture was stirred at room temperature till the reaction completes, as monitored by TLC. The resulting solution was concentrated, to the residue was added water (10 mL) and ethyl acetate (10 mL), pH adjusted to 6.0 with 10percent KHSO4 and stirred for 5 minutes. The organic layer was removed and the aqueous layer was acidified to pH 2.0 with 10percent KHSO4 at 0-5°C and extracted with ethyl acetate (2 x 10 mL). The combined organic layers were washed with 5percent NaHCO3 solution, water, brine and dried over anhydrous Na2SO4. The ethyl acetate layer was concentrated and the residue was crystallized from EtOAc/ n-hexane (2:8) mixture to give the product as a white solid (1.53g, 95percent yield).
Reference: [1] Synthetic Communications, 2017, vol. 47, # 22, p. 2127 - 2132
  • 5
  • [ 24424-99-5 ]
  • [ 139377-27-8 ]
  • [ 57292-44-1 ]
Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 6, p. 1744 - 1752
  • 6
  • [ 2019-34-3 ]
  • [ 57292-44-1 ]
Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 6, p. 1744 - 1752
  • 7
  • [ 1027659-22-8 ]
  • [ 57292-44-1 ]
Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 6, p. 1744 - 1752
  • 8
  • [ 139377-25-6 ]
  • [ 57292-44-1 ]
Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 6, p. 1744 - 1752
  • 9
  • [ 139377-26-7 ]
  • [ 57292-44-1 ]
Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 6, p. 1744 - 1752
  • 10
  • [ 123795-38-0 ]
  • [ 57292-44-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 19, p. 5607 - 5612
  • 11
  • [ 57292-44-1 ]
  • [ 218608-96-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 18, p. 4759 - 4762
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 57292-44-1 ]

Amino Acid Derivatives

Chemical Structure| 114873-03-9

[ 114873-03-9 ]

Boc-Phe(3-Cl)-OH

Similarity: 0.99

Chemical Structure| 80102-25-6

[ 80102-25-6 ]

Boc-D-Phe(3-Cl)-OH

Similarity: 0.99

Chemical Structure| 80741-39-5

[ 80741-39-5 ]

Boc-Phe(3,4-DiCl)-OH

Similarity: 0.97

Chemical Structure| 114873-13-1

[ 114873-13-1 ]

Boc-D-Phe(3,4-Cl2)-OH

Similarity: 0.97

Chemical Structure| 80102-23-4

[ 80102-23-4 ]

(R)-2-((tert-Butoxycarbonyl)amino)-3-(2-chlorophenyl)propanoic acid

Similarity: 0.95