(R)-2-Acetamido-3-(4-chlorophenyl)propanoic acid

Base Information

• Chemical Name: (R)-2-Acetamido-3-(4-chlorophenyl)propanoic acid
• CAS No.: 135270-40-5
• Molecular Formula: C₁₁H₁₂ClNO₃
• Molecular Weight: 241.674
• Hs Code.: 2924299090
• UNII: R21J7Z9S7R
• Nikkaji Number: J898.173F
• Mol file: 135270-40-5.mol

Synonyms:135270-40-5;(R)-2-ACETAMIDO-3-(4-CHLOROPHENYL)PROPANOIC ACID;Acetyl-4-chloro-D-phenylalanine;N-Acetyl-4-chloro-D-phenylalanine;N-Acetyl fenclonine, (R)-;R21J7Z9S7R;N-Acetyl-D-p-chlorophenylalanine;(2R)-2-acetamido-3-(4-chlorophenyl)propanoic acid;D-Phenylalanine, N-acetyl-4-chloro-;(2R)-3-(4-CHLOROPHENYL)-2-ACETAMIDOPROPANOIC ACID;(R)-2-acetamido-3-(4-chlorophenyl)propanoicacid;Ac-p-chloro-D-Phe-OH;UNII-R21J7Z9S7R;SCHEMBL7773675;HLORMWAKCPDIPU-SNVBAGLBSA-N;MFCD00672506;AKOS022180965;EN300-7372384

Chemical Property of (R)-2-Acetamido-3-(4-chlorophenyl)propanoic acid

Chemical Property:

• Vapor Pressure: 4.99E-10mmHg at 25°C
• Boiling Point: 480.1oC at 760 mmHg
• Flash Point: 244.2oC
• PSA: 66.40000
• Density: 1.308g/cm3
• LogP: 1.86270
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 241.0505709
• Heavy Atom Count: 16
• Complexity: 262

Purity/Quality:

99% ^*data from raw suppliers

Acetyl-4-chloro-D-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (R)-2-Acetamido-3-(4-chlorophenyl)propanoic acid

There total 15 articles about (R)-2-Acetamido-3-(4-chlorophenyl)propanoic acid 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: 81.0%

(Z)-N-(1-(4-chlorophenyl)-3-oxoprop-1-en-2-yl)acetamide → (S)-2-acetamido-3-(4-chlorophenyl)propanoic acid (14091-10-2,23434-92-6,135270-40-5,55478-55-2) + (Z)-2-acetamido-3-(4-chlorophenyl)acrylic acid (88681-63-4)

Guidance literature:

With aldehyde dehydrogenase from bovine lens; ene-reductase from Saccharomyces cerevisiae; NADH; In aq. phosphate buffer; at 30 ℃; for 5h; pH=7; Reagent/catalyst; stereoselective reaction; Enzymatic reaction;

DOI:10.1039/c4ob02282c

Reference yield: 73.0%

(Z)-N-(1-(4-chlorophenyl)-3-oxoprop-1-en-2-yl)acetamide → N-(1-(4-chlorophenyl)-3-oxopropan-2-yl)acetamide + (S)-2-acetamido-3-(4-chlorophenyl)propanoic acid (14091-10-2,23434-92-6,135270-40-5,55478-55-2) + (Z)-2-acetamido-3-(4-chlorophenyl)acrylic acid (88681-63-4)

Guidance literature:

With aldehyde dehydrogenase from bovine lens; ene-reductase from Saccharomyces cerevisiae; NADH; In aq. phosphate buffer; at 30 ℃; for 3h; pH=7; Time; stereoselective reaction; Enzymatic reaction;

DOI:10.1039/c4ob02282c

Reference yield: 50.0%

C13H16ClNO3 (875581-67-2) → (R)-2-Acetylamino-3-(4-chloro-phenyl)-propionic acid ethyl ester + (S)-2-acetamido-3-(4-chlorophenyl)propanoic acid (14091-10-2,23434-92-6,135270-40-5,55478-55-2)

Guidance literature:

With water; In ethanol; at 25 ℃; for 4h; optical yield given as %ee; enantioselective reaction; Microbiological reaction;

DOI:10.1016/j.tetasy.2010.02.011

upstream raw materials:

(Z)-2-acetamido-3-(4-chlorophenyl)acrylic acid

acetamide

carbon monoxide

(4-chlorophenyl)acetaldehyde

Downstream raw materials:

(S)-ethyl 2-acetamido-3-(4-chlorophenyl)propanoate

5-[2-acetylamino-3-(4-chloro-phenyl)-propionylamino]-4-oxo-6-phenyl-2-(2-pyridin-2-yl-ethyl)-hexanoic acid [1-carbamoyl-2-(1H-indol-3-yl)ethyl]-amide

Refernces

• 1、 Arava, Veera Reddy,Amasa, Srinivasulu Reddy,Goud Bhatthula, Bharat Kumar,Kompella, Laxmi Srinivas,Matta, Venkata Prasad,Subha. "Asymmetric synthesis of unnatural amino acids and tamsulosin chiral intermediate". supporting information. p. 2892 - 2897. Retrieved 2013/09/02.
• 2、 Stella, Selvaraj,Chadha, Anju. "Resolution of N-protected amino acid esters using whole cells of Candida parapsilosis ATCC 7330". experimental part. p. 457 - 460. Retrieved 2010/06/21.