TERT-BUTOXYCARBONYLAMINO-PHENYL-ACETIC ACID

Base Information

• Chemical Name: TERT-BUTOXYCARBONYLAMINO-PHENYL-ACETIC ACID
• CAS No.: 3601-66-9
• Molecular Formula: C₁₃H₁₇NO₄
• Molecular Weight: 251.282
• Hs Code.: 2924299090
• Mol file: 3601-66-9.mol

Synonyms:Glycine,N-carboxy-2-phenyl-, N-tert-butyl ester (7CI);2-[[[(1,1-Dimethylethyl)oxy]carbonyl]amino]-2-(phenyl)acetic acid;N-BOC-phenylglycine; N-tert-Butoxycarbonyl-DL-phenylglycine;tert-Butoxycarbonylphenylglycine

Chemical Property of TERT-BUTOXYCARBONYLAMINO-PHENYL-ACETIC ACID

Chemical Property:

• Melting Point: 111-112℃
• Boiling Point: 407.2±38.0 °C(Predicted)
• PKA: 3.51±0.10(Predicted)
• PSA: 75.63000
• Density: 1.182±0.06 g/cm3(Predicted)
• LogP: 2.72790
• Storage Temp.: 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

2-[(2-Methylpropan-2-yl)oxycarbonylamino]-2-phenylaceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of TERT-BUTOXYCARBONYLAMINO-PHENYL-ACETIC ACID

There total 24 articles about TERT-BUTOXYCARBONYLAMINO-PHENYL-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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + phenylglycin (2835-06-5) → 2-(tert-butoxycarbonylamino)-2-phenylacetic acid (2900-27-8,3601-66-9,14675-97-9,33125-05-2)

Guidance literature:

With sodium hydroxide; sodium hydrogencarbonate; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1002/ejoc.200400105

Reference yield: 83.0%

carbon dioxide (124-38-9,18923-20-1) + tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate (155396-71-7) → 2-(tert-butoxycarbonylamino)-2-phenylacetic acid (2900-27-8,3601-66-9,14675-97-9,33125-05-2)

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: 79.0%

carbon dioxide (124-38-9,18923-20-1) + N-tert-butoxycarbonylbenzylamine (42116-44-9) → 2-(tert-butoxycarbonylamino)-2-phenylacetic acid (2900-27-8,3601-66-9,14675-97-9,33125-05-2)

Guidance literature:

With sec.-butyllithium; In tetrahydrofuran; 1.) 4 h, -50 deg C;

DOI:10.1016/S0040-4039(00)73726-9

upstream raw materials:

tert-Butyl 4-nitrophenyl carbonate

phenylglycin

carbon dioxide

N-tert-butoxycarbonylbenzylamine

Downstream raw materials:

(6R)-7t-((R)-tert-butoxycarbonylamino-phenyl-acetylsulfanyl)-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2,2-trichloro-ethyl ester

6β-((R)-tert-butoxycarbonylamino-phenyl-acetylsulfanyl)-penicillanic acid 2,2,2-trichloro-ethyl ester

(6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

tert-butyl [1-(3-methylphenylcarbamoyl)-1-phenyl-methyl]-carbamate

Refernces

• 1、 Senboku, Hisanori,Minemura, Yoshihito,Suzuki, Yuto,Matsuno, Hidetoshi,Takakuwa, Mayu. "Synthesis ofN-Boc-α-amino Acids from Carbon Dioxide by Electrochemical Carboxylation ofN-Boc-α-aminosulfones". . p. 16077 - 16083. Retrieved 2021/10/12.
• 2、 Li, Jing,Lear, Martin J.,Kwon, Eunsang,Hayashi, Yujiro. "Mechanism of Oxidative Amidation of Nitroalkanes with Oxygen and Amine Nucleophiles by Using Electrophilic Iodine". supporting information. p. 5538 - 5542. Retrieved 2016/04/20.