[2-(1,1-Dimethyl-allyl)-4-oxo-azetidin-1-yl]-acetic acid benzyl ester

Base Information

• Chemical Name: [2-(1,1-Dimethyl-allyl)-4-oxo-azetidin-1-yl]-acetic acid benzyl ester
• CAS No.: 77150-71-1
• Molecular Formula: C₁₇H₂₁NO₃
• Molecular Weight: 287.359
• Mol file: 77150-71-1.mol

Synonyms:[2-(1,1-Dimethyl-allyl)-4-oxo-azetidin-1-yl]-acetic acid benzyl ester

Chemical Property of [2-(1,1-Dimethyl-allyl)-4-oxo-azetidin-1-yl]-acetic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [2-(1,1-Dimethyl-allyl)-4-oxo-azetidin-1-yl]-acetic acid benzyl ester

There total 1 articles about [2-(1,1-Dimethyl-allyl)-4-oxo-azetidin-1-yl]-acetic acid benzyl 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: 96.0%

4-(1,1-dimethyl-prop-2-enyl)-azetidin-2-one (74949-60-3) + Benzyl bromoacetate (5437-45-6) → [2-(1,1-Dimethyl-allyl)-4-oxo-azetidin-1-yl]-acetic acid benzyl ester (77150-71-1)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)92857-0

Reference yield:

[2-(1,1-Dimethyl-allyl)-4-oxo-azetidin-1-yl]-acetic acid benzyl ester (77150-71-1) → (2R,3S,5S)-3-Methanesulfonyloxy-4,4-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (77150-75-5,80434-20-4,81845-13-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) O₃, 2.) Me₂S / 1.) MeOH, -20 deg C; 2.) -20 deg C up to room temp.

2: 52 percent / LiN(TMS)2 / tetrahydrofuran / -78 °C

3: 65 percent / NEt₃ / CH₂Cl₂ / -78 deg C up to room temp.

With dimethylsulfide; ozone; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)92857-0

Reference yield:

[2-(1,1-Dimethyl-allyl)-4-oxo-azetidin-1-yl]-acetic acid benzyl ester (77150-71-1) → (2R,3S,5S)-4,4-Dimethyl-7-oxo-3-trimethylsilanyloxy-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (77150-74-4,82336-01-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) O₃, 2.) Me₂S / 1.) MeOH, -20 deg C; 2.) -20 deg C up to room temp.

2: 52 percent / LiN(TMS)2 / tetrahydrofuran / -78 °C

3: 78 percent

With dimethylsulfide; ozone; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)92857-0

upstream raw materials:

4-(1,1-dimethyl-prop-2-enyl)-azetidin-2-one

Benzyl bromoacetate

Downstream raw materials:

[2-(1,1-Dimethyl-2-oxo-ethyl)-4-oxo-azetidin-1-yl]-acetic acid benzyl ester

(2R,3S,5S)-4,4-Dimethyl-7-oxo-3-trimethylsilanyloxy-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

[2-(1,1-Dimethyl-2-oxo-2-phenyl-ethyl)-4-oxo-azetidin-1-yl]-acetic acid benzyl ester

(2R,3S,5S)-3-Hydroxy-4,4-dimethyl-7-oxo-3-phenyl-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester