2-Tert-butoxycarbonylamino-3-oxo-3-phenyl-propionic acid ethyl ester

Base Information

• Chemical Name: 2-Tert-butoxycarbonylamino-3-oxo-3-phenyl-propionic acid ethyl ester
• CAS No.: 151870-52-9
• Molecular Formula: C16H21NO5
• Molecular Weight: 307.346
• DSSTox Substance ID: DTXSID20450225
• Nikkaji Number: J730.140E
• Mol file: 151870-52-9.mol

Synonyms:151870-52-9;2-TERT-BUTOXYCARBONYLAMINO-3-OXO-3-PHENYL-PROPIONIC ACID ETHYL ESTER;Ethyl 2-((tert-butoxycarbonyl)amino)-3-oxo-3-phenylpropanoate;ethyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxo-3-phenylpropanoate;DTXSID20450225;DVPJXQCIYYLQGB-UHFFFAOYSA-N;BGA87052;MFCD11506034;AKOS015969607;SB33815;CS-0340797;Ethyl N-(tert-butoxycarbonyl)-beta-oxophenylalaninate;2-t-Butoxycarbonylamino-3-oxo-3-phenyl-propionic acid ethyl ester;ethyl 2-{[(tert-butoxy)carbonyl]amino}-3-oxo-3-phenylpropanoate;2-(tert-Butoxycarbonylamino)-3-oxo-3-phenylpropanoic acid ethyl ester;2-tert-Butoxycarbonylamino-3-oxo-3-phenyl-propionic acid ethyl ester, AldrichCPR

Chemical Property of 2-Tert-butoxycarbonylamino-3-oxo-3-phenyl-propionic acid ethyl ester

Chemical Property:

• PSA: 85.19000
• LogP: 2.53010
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 307.14197277
• Heavy Atom Count: 22
• Complexity: 407

Purity/Quality:

98%min ^*data from raw suppliers

2-tert-Butoxycarbonylamino-3-oxo-3-phenyl-propionicacidethylester 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C(=O)C1=CC=CC=C1)NC(=O)OC(C)(C)C

Technology Process of 2-Tert-butoxycarbonylamino-3-oxo-3-phenyl-propionic acid ethyl ester

There total 7 articles about 2-Tert-butoxycarbonylamino-3-oxo-3-phenyl-propionic acid ethyl ester 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: 91.0%

(benzoyl-tert-butoxycarbonyl-amino)-acetic acid ethyl ester → ethyl-2-((tert-butoxycarbonyl)amino)-3-oxo-3-phenylpropanoate (151870-52-9)

Guidance literature:

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

DOI:10.1016/S0040-4039(98)01093-4

Reference yield: 85.0%

benzoyl chloride (98-88-4) + 2-{[(tert-butoxy)carbonyl]amino}-3-ethoxy-3-oxopropanoic acid (137686-07-8,137401-45-7) → ethyl-2-((tert-butoxycarbonyl)amino)-3-oxo-3-phenylpropanoate (151870-52-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -80 - -50 ℃; for 2h;

DOI:10.1055/s-1993-25933

Reference yield: 63.0%

tert-butyl carbazate (4248-19-5) + ethyl 2-diazo-3-oxo-3-phenylpropanoate (28383-65-5) → ethyl-2-((tert-butoxycarbonyl)amino)-3-oxo-3-phenylpropanoate (151870-52-9)

Guidance literature:

With rhodium (II) octanoate dimer; In dichloromethane;

DOI:10.1016/j.tetasy.2004.10.005

upstream raw materials:

benzoyl chloride

2-{[(tert-butoxy)carbonyl]amino}-3-ethoxy-3-oxopropanoic acid

tert-butyl carbazate

ethyl 2-diazo-3-oxo-3-phenylpropanoate

Downstream raw materials:

(2S,3S)-ethyl-2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-phenylpropanoate

C₁₆H₂₃NO₅

tert-butyl (4S,5R)-4-hydroxymethyl-2,2-dimethyl-5-phenyl-1,3-oxazolidin-3-carboxylate

tert-butyl (1,3-dihydroxy-1-phenylpropan-2-yl)carbamate

Refernces

• 1、 Hara, Osamu,Ito, Masao,Hamada, Yasumasa. "Novel N→C acyl migration reaction of acyclic imides: A facile method for α-aminoketones and β-aminoalcohols". . p. 5537 - 5540. Retrieved 1998.
• 2、 Schmidt,Griesser,Lieberknecht,Schmidt,Grather. "Synthesis of α-acylamino-β-oxo acid esters". . p. 765 - 766. Retrieved 2007/10/02.