Acetamide, N-[2-(acetyloxy)-2-(4-chlorophenyl)ethyl]-, (S)-

Base Information

• Chemical Name: Acetamide, N-[2-(acetyloxy)-2-(4-chlorophenyl)ethyl]-, (S)-
• CAS No.: 149285-94-9
• Molecular Formula: C₁₂H₁₄ClNO₃
• Molecular Weight: 255.701
• DSSTox Substance ID: DTXSID101190653
• Mol file: 149285-94-9.mol

Synonyms:DTXSID101190653;Acetamide, N-[2-(acetyloxy)-2-(4-chlorophenyl)ethyl]-, (S)-;149285-94-9

Chemical Property of Acetamide, N-[2-(acetyloxy)-2-(4-chlorophenyl)ethyl]-, (S)-

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 255.0662210
• Heavy Atom Count: 17
• Complexity: 275

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Acetamide, N-[2-(acetyloxy)-2-(4-chlorophenyl)ethyl]-, (S)-

There total 3 articles about Acetamide, N-[2-(acetyloxy)-2-(4-chlorophenyl)ethyl]-, (S)- 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: 41.0%

vinyl acetate (108-05-4,9003-20-7) + N-(4-chloro-β-hydroxy-phenethyl)-acetamide (149342-40-5) → Acetic acid (S)-2-acetylamino-1-(4-chloro-phenyl)-ethyl ester (149285-94-9)

Guidance literature:

With 4 A molecular sieve; In tetrahydrofuran; hexane; at 25 ℃; for 168h; lipase from Pseudomonas cepacia;

DOI:10.1246/bcsj.66.1216

Reference yield:

N-(2-(4-chlorophenyl)-2-oxoethyl)acetamide (6660-08-8) → Acetic acid (S)-2-acetylamino-1-(4-chloro-phenyl)-ethyl ester (149285-94-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / NaBH₄ / ethanol / 6 h / 0 °C

2: 41 percent / 4 Angstroem sieves / hexane; tetrahydrofuran / 168 h / 25 °C / lipase from Pseudomonas cepacia

With sodium tetrahydroborate; 4 A molecular sieve; In tetrahydrofuran; ethanol; hexane;

DOI:10.1246/bcsj.66.1216

Reference yield:

4-chlorophenacylamine hydrochloride (5467-71-0) → Acetic acid (S)-2-acetylamino-1-(4-chloro-phenyl)-ethyl ester (149285-94-9)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 10 h / Ambient temperature

2: 85 percent / NaBH₄ / ethanol / 6 h / 0 °C

3: 41 percent / 4 Angstroem sieves / hexane; tetrahydrofuran / 168 h / 25 °C / lipase from Pseudomonas cepacia

With pyridine; sodium tetrahydroborate; 4 A molecular sieve; In tetrahydrofuran; ethanol; hexane;

DOI:10.1246/bcsj.66.1216

upstream raw materials:

vinyl acetate

N-(4-chloro-β-hydroxy-phenethyl)-acetamide

N-(2-(4-chlorophenyl)-2-oxoethyl)acetamide

4-chlorophenacylamine hydrochloride

Downstream raw materials:

(S)-(+)-2-amino-1-(p-chlorophenyl)ethanol