Boc-D-Phenylglycine

Base Information

• Chemical Name: Boc-D-Phenylglycine
• CAS No.: 33125-05-2
• Molecular Formula: C13H17NO4
• Molecular Weight: 251.282
• Hs Code.: 29242990
• European Community (EC) Number: 834-862-1
• UNII: 4PFG3246TW
• DSSTox Substance ID: DTXSID30373158
• Nikkaji Number: J703.280C
• Wikidata: Q72450283
• Mol file: 33125-05-2.mol

Synonyms:Benzeneaceticacid, a-[[(1,1-dimethylethoxy)carbonyl]amino]-,(R)-;(R)-N-Boc-2-amino-2-phenylaceticacid;(R)-[(tert-Butoxycarbonyl)amino]phenylethanoicacid;BOC-D-Phg-OH;D-2-tert-Butoxycarboxamido-2-phenylacetic acid;N-(tert-Butoxycarbonyl)-D-2-phenylglycine;N-tert-Butyloxycarbonyl-D-phenylglycine;

Chemical Property of Boc-D-Phenylglycine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 88-91 °C
• Refractive Index: -140 ° (C=1, EtOH)
• Boiling Point: 407.2 °C at 760 mmHg
• PKA: 3.51±0.10(Predicted)
• Flash Point: 200.1 °C
• PSA: 66.84000
• Density: 1.182 g/cm³
• LogP: 2.51270
• Storage Temp.: Store at RT.
• Solubility.: DMSO, Methanol
• Water Solubility.: Insoluble in water. Slightly soluble in DMSO and methanol.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 251.11575802
• Heavy Atom Count: 18
• Complexity: 303

Purity/Quality:

99% ^*data from raw suppliers

(αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]-benzeneaceticAcid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(C1=CC=CC=C1)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](C1=CC=CC=C1)C(=O)O
• Uses: It is a reagent of choice for assignment of absolute configuration of chiral primary amines by 1H NMR, giving better results than Mosher's acid ((R)-(+)-?-Methoxy-?-(trifluoromethyl)-phenyl-acetic acid. αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]-benzeneacetic Acid is D-(+)-2-Phenylglycine with Boc protecting group. (αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]-benzeneacetic Acid is used as part of a catalyst combination to catalyze regioselective [4 + 2] cycloadditions of β-substituted cyclic enones and polyconjugated malononitriles. It can also be used to catalyze stereoselective preparation of polyfunctional nitrocyclohexene carboxaldehydes.

Technology Process of Boc-D-Phenylglycine

There total 76 articles about Boc-D-Phenylglycine 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%

(R)-phenylglycine (875-74-1) + 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) → Boc-D-Phg-OH (33125-05-2)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; for 18h;

DOI:10.1016/j.bmc.2004.07.034

Reference yield: 89.0%

(R)-phenylglycine (875-74-1) + tert-butyl (2,4-dioxo-3-azaspiro[5,5]undecan-3-yl) carbonate → Boc-D-Phg-OH (33125-05-2)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 25 ℃; for 12h;

DOI:10.1080/00397911.2017.1366525

Reference yield: 85.0%

tert-butyl [(1S)-1-phenylprop-2-en-1-yl]imidocarbonate (956101-46-5) → Boc-D-Phg-OH (33125-05-2)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile;

DOI:10.1016/j.tetlet.2007.08.009

upstream raw materials:

tert-Butyl 4-nitrophenyl carbonate

phenylglycin

carbon dioxide

N-tert-butoxycarbonylbenzylamine

Downstream raw materials:

(2-Oxo-1-phenyl-2-pyrrolidin-1-yl-ethyl)-carbamic acid tert-butyl ester

N-(tert-butoxycarbonyl)-D-phenylglycine N-succinimido ester

(methoxy-phenyl-methyl)-carbamic acid tert-butyl ester

(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (R)-2-<(tert-butoxycarbonyl)amino>-2-phenylacetate

Refernces

• 1、 Armani, Elisabetta,Rizzi, Andrea,Capaldi, Carmelida,De Fanti, Renato,Delcanale, Maurizio,Villetti, Gino,Marchini, Gessica,Pisano, Anna Rita,Pitozzi, Vanessa,Pittelli, Maria Gloria,Trevisani, Marcello,Salvadori, Michela,Cenacchi, Valentina,Puccini, Paola,Amadei, Francesco,Pappani, Alice,Civelli, Maurizio,Patacchini, Riccardo,Baker-Glenn, Charles A.G.,Van De Po?l, Hervé,Blackaby, Wesley P.,Nash, Kevin,Amari, Gabriele. "Discovery of M3Antagonist-PDE4 Inhibitor Dual Pharmacology Molecules for the Treatment of Chronic Obstructive Pulmonary Disease". supporting information. p. 9100 - 9119. Retrieved 2021/07/19.
• 2、 -. "ALLOSTERIC EGFR INHIBITORS AND METHODS OF USE THEREOF". Page/Page column 62-63; 90. . Retrieved 2021/01/22.