(R)-Azidophenylacetic acid

Base Information

• Chemical Name: (R)-Azidophenylacetic acid
• CAS No.: 29125-25-5
• Molecular Formula: C8H7 N3 O2
• Molecular Weight: 177.162
• European Community (EC) Number: 249-455-9
• DSSTox Substance ID: DTXSID80183385
• Nikkaji Number: J52.471I
• Wikidata: Q83054163
• Mol file: 29125-25-5.mol

Synonyms:(R)-Azidophenylacetic acid;29125-25-5;(2R)-2-azido-2-phenylacetic acid;EINECS 249-455-9;DTXSID80183385;AKOS006274688;NS00028639;5,6-DICHLORO-4-HYDROXY-3-METHOXYBENZOICACID

Chemical Property of (R)-Azidophenylacetic acid

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 87.05000
• Density: g/cm³
• LogP: 1.57536
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 177.053826475
• Heavy Atom Count: 13
• Complexity: 230

Purity/Quality:

99% ^*data from raw suppliers

D-(-)-ALPHA-AZIDO PHENYLACETIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C(=O)O)N=[N+]=[N-]
• Isomeric SMILES: C1=CC=C(C=C1)[C@H](C(=O)O)N=[N+]=[N-]

Technology Process of (R)-Azidophenylacetic acid

There total 10 articles about (R)-Azidophenylacetic 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: 97.0%

(3(2R),4S)-3-(2-azido-1-oxo-2-phenethyl)-4-(phenylmethyl)-2-oxazolidinone (113543-46-7) → (R)-2-azido-2-phenylacetic acid (29125-25-5,3380-95-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 0.5h;

Reference yield: 85.0%

(S)-2-phenylglycine (2935-35-5) → (R)-2-azido-2-phenylacetic acid (29125-25-5,3380-95-8)

Guidance literature:

With triflic azide; potassium carbonate; copper(II) sulfate; In methanol; dichloromethane; water; at 20 ℃;

DOI:10.1021/ol0155485

Reference yield:

(S)-4-benzyl-3-phenylacetyl-2-oxazolidinone (104266-89-9) → (R)-2-azido-2-phenylacetic acid (29125-25-5,3380-95-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Bu₂BOTf, R₃N, 2.) NBS / 2.) CH₂Cl₂, -78 deg C, 75 min.

2: tetramethylguanidinium azide / CH₂Cl₂ / 3 h / 0 °C / var.: NaN₃, DMF or DMSO, 0 deg C

3: 97 percent / LiOH / tetrahydrofuran; H₂O / 0.5 h / 0 °C

With lithium hydroxide; N-Bromosuccinimide; di-n-butylboryl trifluoromethanesulfonate; tetramethylguanidinum azide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0040-4039(00)95305-X

upstream raw materials:

(3(2R),4S)-3-(2-azido-1-oxo-2-phenethyl)-4-(phenylmethyl)-2-oxazolidinone

(+/-)-2-azido-2-phenylacetamide

(R)-phenylglycine

(R)-1,1,1-trichloro-2-phenylethan-2-ol

Downstream raw materials:

Diphenylmethyl (6R,7R)-7-[(R)-2-Azido-2-phenylacetamido]-3-(3,4-diacetoxybenzoyloxy)methylceph-3-em-4-carboxylate

(2R,3'S,5R,5'R)-benzyl 1-formyl-2',2'-dimethyl-4-oxo-5-phenylspiro-3'-carboxylate

(2R,3'S,5S,5'R)-benzyl 1-formyl-2',2'-dimethyl-4-oxo-5-phenylspiro-3'-carboxylate

(6S)-benzyl 6-<(S)-2-amino-2-phenylacetamido>-6-(methylthio)penicillanate

Refernces

• 1、 Mellin-Morliere, Christelle,Aitken, David J.,Bull, Steven D.,Davies, Stephen G.,Husson, Henri-Philippe. "A practical asymmetric synthesis of homochiral α-arylglycines". . p. 149 - 155. Retrieved 2007/10/03.
• 2、 Tornoe, Christian W.,Sonke, Theo,Maes, Ilse,Schoemaker, Hans E.,Meldal, Morten. "Enzymatic and chiral HPLC resolution of α-azido acids and amides". . p. 1239 - 1248. Retrieved 2007/10/03.