2-[Methyl(phenylmethoxycarbonyl)amino]-3-phenylpropanoic acid

Base Information

• Chemical Name: 2-[Methyl(phenylmethoxycarbonyl)amino]-3-phenylpropanoic acid
• CAS No.: 2899-07-2
• Molecular Formula: C18H19NO4
• Molecular Weight: 313.353
• Hs Code.: 29225090
• NSC Number: 135129
• Mol file: 2899-07-2.mol

Synonyms:Cbz-N-methyl-DL-phenylalanine;81134-79-4;2-[methyl(phenylmethoxycarbonyl)amino]-3-phenylpropanoic acid;MFCD00153393;NSC135129;N-Z-N-Methyl-L-phenylalanine;SCHEMBL8067076;2-[benzyloxycarbonyl(methyl)amino]-3-phenyl-propanoic acid;NSC-135129;PB48205;N-benzyloxycarbonyl-N-methylphenylalanine;SY055794;C78485;EN300-6748101;A819708;2-{[(BENZYLOXY)CARBONYL](METHYL)AMINO}-3-PHENYLPROPANOIC ACID

Chemical Property of 2-[Methyl(phenylmethoxycarbonyl)amino]-3-phenylpropanoic acid

Chemical Property:

• Vapor Pressure: 3.23E-10mmHg at 25°C
• Melting Point: 67.0 to 71.0 °C
• Refractive Index: 1.588
• Boiling Point: 484.96 °C at 760 mmHg
• Flash Point: 247.095 °C
• PSA: 66.84000
• Density: 1.23 g/cm³
• LogP: 2.95090
• Storage Temp.: Store at RT.
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 313.13140809
• Heavy Atom Count: 23
• Complexity: 387

Purity/Quality:

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

Cbz-N-methyl-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C(CC1=CC=CC=C1)C(=O)O)C(=O)OCC2=CC=CC=C2

Technology Process of 2-[Methyl(phenylmethoxycarbonyl)amino]-3-phenylpropanoic acid

There total 15 articles about 2-[Methyl(phenylmethoxycarbonyl)amino]-3-phenylpropanoic 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: 98.0%

(4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester (55740-07-3) → (S)-N-benzyloxycarbonyl-N-methyl-phenyl alanine (2899-07-2)

Guidance literature:

With chloro-trimethyl-silane; sodium cyanoborohydride; In acetonitrile; for 0.0833333h; Ambient temperature;

DOI:10.1246/cl.1999.299

Reference yield: 94.0%

N-Cbz-L-Phe (1161-13-3) + dimethyl sulfate (77-78-1) → (S)-N-benzyloxycarbonyl-N-methyl-phenyl alanine (2899-07-2)

Guidance literature:

With potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4020(98)01042-4

Reference yield: 92.0%

methyl (S)-2-(benzyloxycarbonyl-methyl-amino)-3-phenylpropionate (24164-73-6) → (S)-N-benzyloxycarbonyl-N-methyl-phenyl alanine (2899-07-2)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 65 ℃; for 2h;

DOI:10.1248/cpb.48.114

upstream raw materials:

N-Methyl-L-phenylalanine

benzyl chloroformate

(4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester

N-Cbz-L-Phe

Downstream raw materials:

Cbz-(Me)Phe-Ot-Bu

benzyl (1S)-1-benzyl-2-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-2-oxoethyl(methyl)carbamate

phenylmethyl [(1S)-3-diazo-2-oxo-1-(phenylmethyl)propyl]methylcarbamate

C₂₂H₂₁F₆NO₃

Refernces

• 1、 Hanessian, Stephen,Jennequin, Thomas,Boyer, Nicolas,Babonneau, Vincent,Soma, Udaykumar,Mannoury La Cour, Clotilde,Millan, Mark J.,De Nanteuil, Guillaume. "Design, synthesis, and optimization of balanced dual NK1/NK 3 receptor antagonists". supporting information. p. 550 - 555. Retrieved 2014/06/09.
• 2、 Sun, Dequn,Zhang, Lingzi,Wang, Jin. "Synthesis of N-methyl L-phenylalanine for total synthesis of pepticinnamin e". experimental part. p. 319 - 322. Retrieved 2012/09/07.