p-nitrobenzyl (2S,3S)-2-hydroxymethyl-4-oxo-3-(phenylacetamido)azetidine-1-acetate

Base Information

• Chemical Name: p-nitrobenzyl (2S,3S)-2-hydroxymethyl-4-oxo-3-(phenylacetamido)azetidine-1-acetate
• CAS No.: 128791-76-4
• Molecular Formula: C₂₁H₂₁N₃O₇
• Molecular Weight: 427.414
• Mol file: 128791-76-4.mol

Synonyms:p-nitrobenzyl (2S,3S)-2-hydroxymethyl-4-oxo-3-(phenylacetamido)azetidine-1-acetate

Chemical Property of p-nitrobenzyl (2S,3S)-2-hydroxymethyl-4-oxo-3-(phenylacetamido)azetidine-1-acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrobenzyl (2S,3S)-2-hydroxymethyl-4-oxo-3-(phenylacetamido)azetidine-1-acetate

There total 6 articles about p-nitrobenzyl (2S,3S)-2-hydroxymethyl-4-oxo-3-(phenylacetamido)azetidine-1-acetate 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: 95.0%

[(2S,3S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester (192517-62-7) → p-nitrobenzyl (2S,3S)-2-hydroxymethyl-4-oxo-3-(phenylacetamido)azetidine-1-acetate (128791-76-4)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1039/a700650k

Reference yield:

p-nitrobenzyl (2S,3S)-3-azido-2-(tert-butyldimethylsiloxymethyl)-4-oxoazetidine-1-acetate (128791-75-3) → p-nitrobenzyl (2S,3S)-2-hydroxymethyl-4-oxo-3-(phenylacetamido)azetidine-1-acetate (128791-76-4)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂S, Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 95 percent / conc. aq. HCl / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; hydrogenchloride; hydrogen sulfide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1039/a700650k

Reference yield:

(3S,4S)-3-azido-4-hydroxymethyl-1-(p-nitrobenzylcarbamoylmethyl)azetidin-2-one (104227-75-0) → p-nitrobenzyl (2S,3S)-2-hydroxymethyl-4-oxo-3-(phenylacetamido)azetidine-1-acetate (128791-76-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / imidazole / dimethylformamide / Ambient temperature

2: N₂O₄, NaOAc / CHCl₃ / 1 h / 0 °C

3: 1,2-dichloro-ethane / 3 h / Heating

4: H₂S, Et₃N / CH₂Cl₂ / 1 h / 0 °C

5: pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

6: 95 percent / conc. aq. HCl / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; hydrogen sulfide; sodium acetate; dinitrogen tetraoxide; triethylamine; In tetrahydrofuran; dichloromethane; chloroform; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1039/a700650k

upstream raw materials:

[(2S,3S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester

p-nitrobenzyl (2S,3S)-3-azido-2-(tert-butyldimethylsiloxymethyl)-4-oxoazetidine-1-acetate

(3S,4S)-3-azido-4-hydroxymethyl-1-(p-nitrobenzylcarbamoylmethyl)azetidin-2-one

Downstream raw materials:

p-nitrobenzyl (2S,3S)-2-(imidazol-1-yl)carbonyloxymethyl-4-oxo-3-(phenylacetamido)azetidine-1-acetate