(4S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(1H-imidazol-2-ylamino)-methyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Base Information

• Chemical Name: (4S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(1H-imidazol-2-ylamino)-methyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• CAS No.: 145663-72-5
• Molecular Formula: C₁₄H₁₈N₄O₄
• Molecular Weight: 306.321
• Mol file: 145663-72-5.mol

Synonyms:

Chemical Property of (4S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(1H-imidazol-2-ylamino)-methyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(1H-imidazol-2-ylamino)-methyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid

There total 3 articles about (4S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(1H-imidazol-2-ylamino)-methyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic 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:

(4S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxymethyl-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester (104618-38-4) → (4S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(1H-imidazol-2-ylamino)-methyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid (145663-72-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / DEAD, PPh₃ / toluene / 0.5 h / 20 °C

2: 1) n-Bu₄NF, 2) Pd(PPh₃)4, dimedone / 1) THF, AcOH, 2) THF

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; dimedone; triphenylphosphine; diethylazodicarboxylate; In toluene;

DOI:10.1016/S0040-4039(00)60855-9

Reference yield:

[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-3-hydroxy-1-methyl-2-oxo-propyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid allyl ester (104634-56-2) → (4S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(1H-imidazol-2-ylamino)-methyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid (145663-72-5)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene / 1 h / 110 °C

2: 68 percent / DEAD, PPh₃ / toluene / 0.5 h / 20 °C

3: 1) n-Bu₄NF, 2) Pd(PPh₃)4, dimedone / 1) THF, AcOH, 2) THF

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; dimedone; triphenylphosphine; diethylazodicarboxylate; In toluene;

DOI:10.1016/S0040-4039(00)60855-9

Reference yield:

(4S,5R,6S)-3-{[Allyloxycarbonyl-(1H-imidazol-2-yl)-amino]-methyl}-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester (145663-69-0) → (4S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(1H-imidazol-2-ylamino)-methyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid (145663-72-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; dimedone; Multistep reaction; 1) THF, AcOH, 2) THF;

DOI:10.1016/S0040-4039(00)60855-9

upstream raw materials:

(4S,5R,6S)-3-{[Allyloxycarbonyl-(1H-imidazol-2-yl)-amino]-methyl}-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

(4S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxymethyl-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-3-hydroxy-1-methyl-2-oxo-propyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester