(R)-2-((tert-Butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid

Base Information

• Chemical Name: (R)-2-((tert-Butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid
• CAS No.: 53994-85-7
• Molecular Formula: C13H16ClNO4
• Molecular Weight: 285.727
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID10427446
• Wikidata: Q72448912
• ChEMBL ID: CHEMBL5020232
• Mol file: 53994-85-7.mol

Synonyms:53994-85-7;(R)-2-((tert-Butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid;Boc-D-Phg(4-Cl)-OH;N-Boc-2-(4'-Chlorophenyl)-D-glycine;N-Boc-(4'-chlorophenyl)glycine;(2R)-2-(4-chlorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid;N-Boc-(4-chlorophenyl)glycine;(R)-TERT-BUTOXYCARBONYLAMINO-(4-CHLORO-PHENYL)-ACETIC ACID;SCHEMBL4277192;CHEMBL5020232;DTXSID10427446;MFCD07371720;AKOS015916831;BS-42415;(R)-4-Chloro-alpha-(Boc-amino)benzeneacetic acid;(2R)-[(tert-Butoxycarbonyl)amino](4-chlorophenyl)acetic acid;N-alpha-t-Butyloxycarbonyl-D-4-chlorophenylglycine (Boc-D-Phg(4-Cl)-OH)

Chemical Property of (R)-2-((tert-Butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid

Chemical Property:

• Boiling Point: 438.8 °C at 760 mmHg
• PKA: 3.38±0.10(Predicted)
• Flash Point: 219.2 °C
• PSA: 75.63000
• Density: 1.272g/cm³
• LogP: 3.38130
• Storage Temp.: 2-8°C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 285.0767857
• Heavy Atom Count: 19
• Complexity: 332

Purity/Quality:

97% ^*data from raw suppliers

N-Boc-(4'-Chlorophenyl)glycine 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (R)-2-((tert-Butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid

There total 8 articles about (R)-2-((tert-Butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic 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%

di-tert-butyl dicarbonate (24424-99-5) + 2-(4-Chlorophenyl)glycine (6212-33-5,7292-70-8) → (±)-2-(tert-butoxycarbonyl)-2-(4-chlorophenyl)acetic Acid (53994-85-7)

Guidance literature:

di-tert-butyl dicarbonate; 2-(4-Chlorophenyl)glycine; With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 15h;

With hydrogenchloride; In water; pH=1; Cooling;

Reference yield: 70.0%

carbon dioxide (124-38-9,18923-20-1) + N-(tert-butoxycarbonyl)-α-(phenylsulfonyl)-4-chlorobenzylamine (774225-25-1) → (±)-2-(tert-butoxycarbonyl)-2-(4-chlorophenyl)acetic Acid (53994-85-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In N,N-dimethyl-formamide; at 0 ℃; under 760.051 Torr; Electrochemical reaction;

DOI:10.1021/acs.joc.1c01516

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (R)-2-amino-2-(4-chlorophenyl)acetic acid (43189-37-3,7292-70-8) → (R)-2-((tert-butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid (53994-85-7)

Guidance literature:

di-tert-butyl dicarbonate; (R)-2-amino-2-(4-chlorophenyl)acetic acid; With sodium hydroxide; In water; acetonitrile; at 20 ℃;

With hydrogenchloride; In water; acetonitrile; Acidic conditions;

upstream raw materials:

di-tert-butyl dicarbonate

2-(4-Chlorophenyl)glycine

tert-butyl carbazate

carbon dioxide

Downstream raw materials:

tert-butyl 1-(4-chlorophenyl)-2-hydrazinyl-2-oxoethylcarbamate

(R,S)-[(4-chlorophenyl)-(2,5-dimethyl-2H-pyrazol-3-ylcarbamoyl)methyl]carbamic acid tert-butyl ester

(R,S)-{(4-Chloro-phenyl)-[(5-methyl-thiazol-2-yl)-(2-p-tolyl-ethyl)-carbamoyl]-methyl}-carbamic acid tert-butyl ester

(R,S)-{(4-chloro-phenyl)-[(2,4-dimethyl-thiazol-5-yl)-(2-p-tolyl-ethyl)-carbamoyl]-methyl}-carbamic acid tert-butyl ester