Boc-3-chloro-D-phenylalanine

Base Information

• Chemical Name: Boc-3-chloro-D-phenylalanine
• CAS No.: 80102-25-6
• Molecular Formula: C₁₄H₁₈ClNO₄
• Molecular Weight: 299.754
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID40427297
• Wikidata: Q72448895
• Mol file: 80102-25-6.mol

Synonyms:80102-25-6;Boc-3-chloro-D-phenylalanine;Boc-D-phe(3-Cl)-OH;Boc-D-3-Chlorophenylalanine;(R)-2-((tert-Butoxycarbonyl)amino)-3-(3-chlorophenyl)propanoic acid;(2R)-3-(3-chlorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;D-Phenylalanine, 3-chloro-N-[(1,1-dimethylethoxy)carbonyl]-;Boc-L-phe(3-Cl)-OH;N-(tert-Butoxycarbonyl)-D-3-chlorophenylalanine;N-Boc-3-chloro-D-phenylalanine;(R)-2-(tert-butoxycarbonylamino)-3-(3-chlorophenyl)propanoic acid;MFCD00672516;N-TERT-BUTOXYCARBONYL-D-3-CHLORO PHENYLALANINE;SCHEMBL3553561;DTXSID40427297;RCZHBTHQISEPPP-LLVKDONJSA-N;AKOS015836554;AC-9876;AM82745;CS-W012137;DS-15341;M03178;N10792;Boc-D-Phe(3-Cl)-OH, >=98.0% (HPLC);EN300-3367020;N-(tert-butoxycarbonyl)-3-chloro-D-phenylalanine;J-300383;(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-phenyl)-propionic acid;(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-(3-chlorophenyl)propanoic acid;N-alpha-t-Butyloxycarbonyl-D-3-chlorophenylalanine (Boc-D-Phe(3-Cl)-OH)

Chemical Property of Boc-3-chloro-D-phenylalanine

Chemical Property:

• Vapor Pressure: 5.61E-09mmHg at 25°C
• Melting Point: 110 °C
• Refractive Index: 1.538
• Boiling Point: 452.5 °C at 760 mmHg
• PKA: 3.81±0.10(Predicted)
• Flash Point: 227.5 °C
• PSA: 75.63000
• Density: 1.245 g/cm³
• LogP: 3.25130
• Storage Temp.: Store at 0°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 299.0924357
• Heavy Atom Count: 20
• Complexity: 354

Purity/Quality:

99% ^*data from raw suppliers

Boc-3-chloro-D-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC(=CC=C1)Cl)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=CC(=CC=C1)Cl)C(=O)O

Technology Process of Boc-3-chloro-D-phenylalanine

There total 4 articles about Boc-3-chloro-D-phenylalanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C15H20ClNO4 (1254365-76-8) → ((R)-2-(tert-butoxycarbonyl)amino)-3-(3-chlorophenyl)propanoic acid (114873-03-9,80102-25-6)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; methanol; at 0 ℃; for 6h;

DOI:10.1016/j.bmcl.2010.08.053

Reference yield:

diethyl tert-butoxycarbonylaminomalonate (102831-44-7) → N-tert-butoxycarbonyl-β-(3-chlorophenyl)-D,L-alanine (188814-25-7,114873-03-9,80102-25-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide; hexane / 2 h / 20 °C

1.2: dimethylformamide; hexane / 2 h / 20 °C

2.1: aq. AcOH / 16 h / pH 5 / Heating

With sodium hydride; acetic acid; In hexane; N,N-dimethyl-formamide;

DOI:10.1021/jm010206q

Reference yield:

1-bromomethyl-3-chlorobenzene (766-80-3) → N-tert-butoxycarbonyl-β-(3-chlorophenyl)-D,L-alanine (188814-25-7,114873-03-9,80102-25-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide; hexane / 2 h / 20 °C

1.2: dimethylformamide; hexane / 2 h / 20 °C

2.1: aq. AcOH / 16 h / pH 5 / Heating

With sodium hydride; acetic acid; In hexane; N,N-dimethyl-formamide;

DOI:10.1021/jm010206q

upstream raw materials:

C₁₅H₂₀ClNO₄

diethyl tert-butoxycarbonylaminomalonate

1-bromomethyl-3-chlorobenzene

Downstream raw materials:

(S)-2-amino-3-(3-chlorophenyl)-N-(2-oxo-5-(pyridin-4-yl)-1,2-dihydropyridin-3-yl)propanamide

C₂₁H₂₃BrClN₃O₄

Refernces

• 1、 Greenspan,Clark,Tommasi,Cowen,McQuire,Farley,Van Duzer,Goldberg,Zhou,Du,Fitt,Coppa,Fang,Macchia,Zhu,Capparelli,Goldstein,Wigg,Doughty,Bohacek,Knap. "Identification of dipeptidyl nitriles as potent and selective inhibitors of cathepsin B through structure-based drug design". . p. 4524 - 4534. Retrieved 2007/10/03.