(R)-2-Amino-2-methyl-3-phenylpropanoic acid

Base Information

• Chemical Name: (R)-2-Amino-2-methyl-3-phenylpropanoic acid
• CAS No.: 17350-84-4
• Molecular Formula: C10H13NO2
• Molecular Weight: 179.219
• Hs Code.: 2922499990
• European Community (EC) Number: 635-120-8
• DSSTox Substance ID: DTXSID001313216
• Nikkaji Number: J52.793I
• ChEMBL ID: CHEMBL4250045
• Mol file: 17350-84-4.mol

Synonyms:17350-84-4;(R)-2-Amino-2-methyl-3-phenylpropanoic acid;ALPHA-METHYL-D-PHENYLALANINE;(2R)-2-amino-2-methyl-3-phenylpropanoic acid;CHEMBL4250045;alpha-methyl-D-Phe;ALPHA-BENZYL-D-ALA;D-Phenylalanine, alpha-methyl-;D-ALPHA-METHYL PHENYLALANINE;a-methyl-d-phenylalanine;(R)-2-amimo-2-methyl-3-phenylpropanoic acid;(R)-alpha-Methylphenylalanine;alpha -Methyl-D-phenylalanine;SCHEMBL202327;(R)-alpha-methyl phenylalanine;(r)-alpha-methylphenyl-alanine;HYOWVAAEQCNGLE-SNVBAGLBSA-N;DTXSID001313216;BDBM50463193;MFCD00153491;AKOS016843198;AB04114;AC-4461;CS-W017267;HY-W016551;DS-16370;|A inverted exclamation mark-Benzyl-D-Ala;EN300-755615;F10695;A811521;alpha-Methyl-D-phenylalanine, >=98.0% (HPLC);J-010914

Chemical Property of (R)-2-Amino-2-methyl-3-phenylpropanoic acid

Chemical Property:

• Melting Point: 277-279 °C(Solv: acetone (67-64-1))
• Boiling Point: 312.8 °C at 760 mmHg
• PKA: 2.25±0.10(Predicted)
• Flash Point: 143 °C
• PSA: 63.32000
• Density: 1.166g/cm³
• LogP: 1.73140
• Storage Temp.: Store at RT.
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 187

Purity/Quality:

99% ^*data from raw suppliers

2-Methyl-D-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

Useful:

• Canonical SMILES: CC(CC1=CC=CC=C1)(C(=O)O)N
• Isomeric SMILES: C[C@@](CC1=CC=CC=C1)(C(=O)O)N
• Uses: α-Methyl-D-phenylalanine is used to prepare hippuryl-α-methylphenylalanine and hippuryl-α-methylphenyllactic acid as substrates for carboxypeptidase A. It is also used in the synthesis of high affinity tachykinin NK2 receptor antagonists. 2-Methyl-D-phenylalanine is a derivative of D-Phenylalanine (P319410); the stereoisomer of L-Phenylalanine (P319415) used in the synthesis of Schaeffer’s acid analogs as important structures in tuberculostatic design. These analogs exhibit the ability to inhibit Mycobacterium tuberculosis type II dehydroquinase.

Technology Process of (R)-2-Amino-2-methyl-3-phenylpropanoic acid

There total 106 articles about (R)-2-Amino-2-methyl-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: 100.0%

(R)-2-benzoylamino-2-methyl-3-phenylpropanoic acid (161956-17-8) → (R)-2-amino-2-methyl-3-phenylpropanoic acid (17350-84-4)

Guidance literature:

With hydrogenchloride; for 1.5h; Heating;

DOI:10.1039/b212454h

Reference yield: 90.0%

Sodium; (R)-2-methyl-3-phenyl-2-((S)-1-phenyl-ethylamino)-propionate → (R)-2-amino-2-methyl-3-phenylpropanoic acid (17350-84-4)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; for 12h; under 2585.74 Torr;

DOI:10.1016/S0957-4166(98)00272-9

Reference yield: 90.0%

(R)-methyl 2-benzamido-2-methyl-3-phenylpropanoate (169738-76-5) → (R)-2-amino-2-methyl-3-phenylpropanoic acid (17350-84-4)

Guidance literature:

(R)-methyl 2-benzamido-2-methyl-3-phenylpropanoate; With hydrogenchloride; In 1,4-dioxane; at 100 ℃; for 20h;

With methyloxirane; In ethanol; for 0.5h; Heating;

DOI:10.1016/S0968-0896(00)00006-7

upstream raw materials:

N-trifluoroacetyl-alpha-methyl-d,l-phenylalanine

(R)-(+)-N-Acetyl-α-methyl-phenylalanin

(R)-(-)-methyl 2-amino-2-methyl-3-phenylpropionate

benzyl bromide

Downstream raw materials:

(R)-(-)-methyl 2-amino-2-methyl-3-phenylpropionate

Ac-D-(αMe)Phe-OH oxazol-5(4H)-one

(2R)-(-)-N-<(1,1-dimethylethyl)oxycarbonyl>-2-methyl-3-phenylalanine

3-(5-((R)-2-tert-butoxycarbonylamino-1-phenylpropan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(1-cyanocyclopentyl)-N-((R)-1-(4-fluorophenyl)ethyl)benzamide

Refernces

• 1、 Alonso,Davies. "Enantiospecific conversion of (S)-alanine to (R)-α-methyl phenylalanine". . p. 353 - 356. Retrieved 1995.
• 2、 Blesl, Julia,Trobe, Melanie,Anderl, Felix,Breinbauer, Rolf,Strohmeier, Gernot A.,Fesko, Kateryna. "Application of Threonine Aldolases for the Asymmetric Synthesis of α-Quaternary α-Amino Acids". . p. 3453 - 3458. Retrieved 2018/07/30.
• 3、 Remelli, Maurizio,Faccini, Stefania,Conato, Chiara. "Chiral ligand-exchange resolution of underivatized amino acids on a dynamically modified stationary phase for RP-HPTLC". . p. 313 - 318. Retrieved 2014/06/09.