Tert-butyl (2-oxoethyl)phenylcarbamate

Base Information

• Chemical Name: Tert-butyl (2-oxoethyl)phenylcarbamate
• CAS No.: 141222-95-9
• Molecular Formula: C13H17NO3
• Molecular Weight: 235.283
• DSSTox Substance ID: DTXSID80569468
• Wikidata: Q82456626
• Mol file: 141222-95-9.mol

Synonyms:tert-butyl (2-oxoethyl)phenylcarbamate;Boc-phenylglycinal;141222-95-9;SCHEMBL1974012;DTXSID80569468;WFDSOPIDPCMTCA-UHFFFAOYSA-N;(2-oxo-ethyl)-phenyl-carbamic acid tert-butyl ester

Chemical Property of Tert-butyl (2-oxoethyl)phenylcarbamate

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 235.12084340
• Heavy Atom Count: 17
• Complexity: 264

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Tert-butyl (2-oxoethyl)phenylcarbamate

There total 4 articles about Tert-butyl (2-oxoethyl)phenylcarbamate 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%

N-phenyl-N-(tert-butoxtcarbonyl)-2-aminoethanol (121492-10-2) → tert-butyl (formylmethyl)(phenyl)carbamate (141222-95-9)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -60 - 0 ℃;

DOI:10.1021/jo071124y

Reference yield: 47.0%

tert-butyl allyl(phenyl)carbamate (169268-95-5) → N-t-butoxycarbonyl L-phenylglycine (150806-61-4) + tert-butyl (formylmethyl)(phenyl)carbamate (141222-95-9)

Guidance literature:

With sodium periodate; RuO₂/BaTi₄O₉; In phosphate buffer; ethyl acetate; at 20 ℃; for 29h; pH=6.88;

DOI:10.1055/s-2007-992378

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (formylmethyl)(phenyl)carbamate (141222-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / dioxane / 36 h / 50 °C

2: 94 percent / oxalyl chloride; DMSO; iPr₂NEt / CH₂Cl₂ / -60 - 0 °C

With oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane; 2: Swern oxidation;

DOI:10.1021/jo071124y

upstream raw materials:

N-phenyl-N-(tert-butoxtcarbonyl)-2-aminoethanol

di-tert-butyl dicarbonate

2-Anilinoethanol

tert-butyl allyl(phenyl)carbamate

Downstream raw materials:

C₁₇H₂₃NO₄

N-Boc-2-hydroxy-1-phenyl-hex-5-enyl-1-amine

tert-butyl (3R,4R)-4-({2-[(tert-butoxycarbonyl)(phenyl)amino]ethyl}amino)-3-(3,4-dichlorophenyl)piperidine-1-carboxylate

tert-butyl (3R,4R)-3-(3,4-dichlorophenyl)-4-{[2-(phenylamino)ethyl]amino}piperidine-1-carboxylate