(R)-2-(((Benzyloxy)carbonyl)amino)-2-phenylacetic acid

Base Information

• Chemical Name: (R)-2-(((Benzyloxy)carbonyl)amino)-2-phenylacetic acid
• CAS No.: 17609-52-8
• Molecular Formula: C16H15NO4
• Molecular Weight: 285.299
• Hs Code.: 29242990
• European Community (EC) Number: 241-582-8
• DSSTox Substance ID: DTXSID40938757
• Nikkaji Number: J72.297I
• Wikidata: Q72516367
• Mol file: 17609-52-8.mol

Synonyms:Z-D-Phg-OH;17609-52-8;(R)-2-(((Benzyloxy)carbonyl)amino)-2-phenylacetic acid;Cbz-D-(-)-Phenylglycine;(2r)-{[(benzyloxy)carbonyl]amino}(phenyl)acetic acid;EINECS 241-582-8;(2R)-2-phenyl-2-(phenylmethoxycarbonylamino)acetic acid;N-Carbobenzoxy-D-2-phenylglycine;(R)-N-Benzyloxycarbonyl-alpha-carboxybenzylamine;(R)-(((Phenylmethoxy)carbonyl)amino)phenylacetic acid;(R)-2-(BENZYLOXYCARBONYLAMINO)-2-PHENYLACETIC ACID;(R)-[[(phenylmethoxy)carbonyl]amino]phenylacetic acid;MFCD00021703;Z-D-2-phenylglycine;CBZ-D-PHENYLGLYCINE;SCHEMBL1362502;(R)-2-(((Benzyloxy)carbonyl)amino)-2-phenylaceticacid;DTXSID40938757;AKOS010385698;(?)-N-Benzyloxycarbonyl-D-phenylglycine;AC-26600;AM808143;AS-19073;HY-75332;Z-D-Phg-OH, >=99.0% (HPLC);C2566;CS-0005785;EN300-122133;N-ALPHA-BENZYLOXYCARBONYL-D-PHENYLGLYCINE;A812149;J-300367;Q-101729;(2R)-2-{[(benzyloxy)carbonyl]amino}-2-phenylacetic acid;(2R)-2-{[(benzyloxy)carbonyl]amino}-2-phenylethanoic acid;{[(Benzyloxy)(hydroxy)methylidene]amino}(phenyl)acetic acid;Benzeneacetic acid, alpha-[[(phenylmethoxy)carbonyl]amino]-, (alphaR)-

Chemical Property of (R)-2-(((Benzyloxy)carbonyl)amino)-2-phenylacetic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 130.0 to 135.0 °C
• Refractive Index: 1.626
• Boiling Point: 495.3 ºC at 760 mmHg
• PKA: 3.49±0.10(Predicted)
• Flash Point: 253.4 ºC
• PSA: 75.63000
• Density: 1.275 g/cm³
• LogP: 3.12960
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethanol (Sparingly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 285.10010796
• Heavy Atom Count: 21
• Complexity: 346

Purity/Quality:

99% ^*data from raw suppliers

Cbz-D-(-)-Phenylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(C2=CC=CC=C2)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@H](C2=CC=CC=C2)C(=O)O

Technology Process of (R)-2-(((Benzyloxy)carbonyl)amino)-2-phenylacetic acid

There total 35 articles about (R)-2-(((Benzyloxy)carbonyl)amino)-2-phenylacetic 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: 94.0%

(S)-ethyll 2-(benzyloxycarbonylamino)-2-phenylacetate (219323-43-0) → (S)-N-(benzyloxycarbonyl)phenylglycine (5491-18-9,17609-52-8,53990-33-3,60584-76-1)

Guidance literature:

With potassium trimethylsilonate; In tetrahydrofuran; at 20 ℃; for 16h;

Reference yield: 92.0%

(S)-2-phenylglycine (2935-35-5) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-N-(benzyloxycarbonyl)phenylglycine (5491-18-9,17609-52-8,53990-33-3,60584-76-1)

Guidance literature:

fipronilβ-cyclodextrin; In various solvent(s); at 20 ℃; for 0.166667h; pH=8;

DOI:10.1016/j.tetlet.2006.06.162

Reference yield: 86.0%

(S)-methyl 2-(benzyloxycarbonylamino)-2-phenylacetate (147780-61-8) → (S)-N-(benzyloxycarbonyl)phenylglycine (5491-18-9,17609-52-8,53990-33-3,60584-76-1)

Guidance literature:

With 2C₃₃H₃₇N*H₂O₇S₂; water; at 80 ℃; for 9h; optical yield given as %ee;

DOI:10.1021/ol301290c

upstream raw materials:

(R)-phenylglycine

benzyl chloroformate

2-(benzyloxycarbonylamino)-2-phenylacetic acid

N-<(Phenylmethoxy)carbonyl>-D-phenylglycine 2-iodoethyl ester

Downstream raw materials:

6β-((R)-2-benzyloxycarbonylamino-2-phenyl-acetylamino)-6α-methylsulfanyl-penicillanic acid benzyl ester

(R)-1-pyrrolidine

(S)-1-pyrrolidine

((S)-2-Oxo-1-phenyl-2-piperidin-1-yl-ethyl)-carbamic acid benzyl ester

Refernces

• 1、 Mousa, Mai H. A.,Ahmed, Nermin S.,Schwedtmann, Kai,Frakolaki, Efseveia,Vassilaki, Niki,Zoidis, Grigoris,Weigand, Jan J.,Abadi, Ashraf H.. "Design and synthesis of novel symmetric fluorene-2,7-diamine derivatives as potent hepatitis C virus inhibitors". . . Retrieved 2021/04/16.
• 2、 Genc, Hayriye Nevin. "Enantioselective Michael reaction of anthrone catalyzed by chiral tetraoxacalix[2]arene[2]triazine derivatives". . p. 21063 - 21069. Retrieved 2019/07/12.