Boc-3,4-dichloro-D-phenylalanine

Base Information

• Chemical Name: Boc-3,4-dichloro-D-phenylalanine
• CAS No.: 114873-13-1
• Molecular Formula: C₁₄H₁₇Cl₂NO₄
• Molecular Weight: 334.199
• Hs Code.: 29242990
• Nikkaji Number: J2.437.573K
• Mol file: 114873-13-1.mol

Synonyms:114873-13-1;Boc-3,4-dichloro-D-phenylalanine;Boc-D-Phe(3,4-Cl2)-OH;(R)-2-((tert-Butoxycarbonyl)amino)-3-(3,4-dichlorophenyl)propanoic acid;D-Phenylalanine, 3,4-dichloro-N-[(1,1-dimethylethoxy)carbonyl]-;(2R)-3-(3,4-dichlorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;N-BOC-D-3,4-DICHLOROPHENYLALANINE;MFCD00151887;Boc-Phe(3,4-Cl2)-OH;N-BOC-3,4-DICHLORO-D-PHENYLALANINE;SCHEMBL1311165;UGZIQCCPEDCGGN-LLVKDONJSA-N;AKOS015836544;AC-9882;AM82044;CS-W011934;DS-7827;HY-W011218;PD196806;F12278;Boc-D-Phe(3,4-Cl2)-OH, >=98.0% (TLC);J-003150;N-tert-Butoxycarbonyl-3,4-dichloro-D-phenylalanine;N-TERT-BUTOXYCARBONYL-D-3,4-DICHLORO PHENYLALANINE;Boc-D-3,4-Dichlorophenylalanine (Boc-D-Phe(3,4-diCl)-OH);(R)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(3,4-DICHLOROPHENYL)PROPANOIC ACID

Chemical Property of Boc-3,4-dichloro-D-phenylalanine

Chemical Property:

• Vapor Pressure: 6.01E-10mmHg at 25°C
• Melting Point: 120°C
• Refractive Index: 1.548
• Boiling Point: 478.1 °C at 760 mmHg
• PKA: 3.75±0.10(Predicted)
• Flash Point: 242.9 °C
• PSA: 75.63000
• Density: 1.323g/cm³
• LogP: 3.90470
• Storage Temp.: -15°C
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 333.0534634
• Heavy Atom Count: 21
• Complexity: 384

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-3,4-dichloro-D-phenylalanine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC(=C(C=C1)Cl)Cl)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=CC(=C(C=C1)Cl)Cl)C(=O)O
• Uses: N-Boc-D-3,4-dichlorophenylalanine is used to prepare fluorinated β-aminoacyl 1,2,4-triazolo[4,3-a]piperazine amides as dipeptidyl peptidase IV inhibitors and antidiabetic agents. It is also used in the synthesis of N-[(R,R)-(E)-1-(3,4-dichlorobenzyl)-3- (2-oxoazepan-3-yl)carbamoyl]allyl-N-methyl-3,5-bis(trifluoromethyl)benzamide as a potent and orally active dual neurokinin NK1/NK2 receptor antagonist.

Technology Process of Boc-3,4-dichloro-D-phenylalanine

There total 2 articles about Boc-3,4-dichloro-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:

C15H19Cl2NO4 → N-Boc-D-3,4-dichlorophenylalanine (114873-13-1,80741-39-5)

Guidance literature:

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

DOI:10.1016/j.bmcl.2010.08.053

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + 2-amino-3-(3,4-dichlorophenyl)propionic acid (5472-67-3,52794-99-7) → 2-tert-butyloxycarbonylamino-3-(3,4-dichlorophenyl)propionic acid (185321-62-4,114873-13-1,80741-39-5)

Guidance literature:

With sodium hydroxide; sodium hydrogencarbonate; In 1,4-dioxane; at 0 - 20 ℃;

DOI:10.1016/0968-0896(96)00185-X

Reference yield: 68.0%

1-amino-1-cyclopropanecarbonitrile hydrochloride (127946-77-4) + Nα-[(tert-butoxy)carbonyl]-3,4-dichloro-L-phenylalanine (114873-13-1,80741-39-5) → Nα-[(tert-butoxy)carbonyl]-N-(1-cyanocyclopropyl)-3,4-dichloro-L-phenylalaninamide

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 22 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b01870

upstream raw materials:

di-tert-butyl dicarbonate

2-amino-3-(3,4-dichlorophenyl)propionic acid

Downstream raw materials:

(S)-3-(3,4-Dichloro-phenyl)-2-ethylamino-propionamide

({[(S)-1-Carbamoyl-2-(3,4-dichloro-phenyl)-ethyl]-ethyl-carbamoyl}-methyl)-carbamic acid tert-butyl ester

[(S)-1-{(R)-1-[({[(S)-1-Carbamoyl-2-(3,4-dichloro-phenyl)-ethyl]-ethyl-carbamoyl}-methyl)-carbamoyl]-4-guanidino-butylcarbamoyl}-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester

ethyl 1-[(R)-2-tert-butoxycarbonylamino-3-(3,4-dichlorophenyl)propionyl]-4-cyclohexylpiperidine-4-carboxylate

Refernces

• 1、 Augelli-Szafran, Corinne E.,Horwell, David C.,Kneen, Clare,Ortwine, Daniel F.,Pritchard, Martyn C.,Purchase, Terri S.,Roth, Bruce D.,Trivedi, Bharat K.,Hill, David,Suman-Chauhan, Nirmala,Webdale, Louise. "Cholecystokinin B antagonists. Synthesis and quantitative structure-activity relationships of a series of C-terminal analogues of CI-988". . p. 1733 - 1745. Retrieved 2007/10/03.