methyl (RS)-3-(benzyloxycarbonylmethyl)-1,2-thiazetidin-2-acetate 1,1-dioxide

Base Information

• Chemical Name: methyl (RS)-3-(benzyloxycarbonylmethyl)-1,2-thiazetidin-2-acetate 1,1-dioxide
• CAS No.: 757237-19-7
• Molecular Formula: C₁₄H₁₇NO₆S
• Molecular Weight: 327.358
• Mol file: 757237-19-7.mol

Synonyms:methyl (RS)-3-(benzyloxycarbonylmethyl)-1,2-thiazetidin-2-acetate 1,1-dioxide

Chemical Property of methyl (RS)-3-(benzyloxycarbonylmethyl)-1,2-thiazetidin-2-acetate 1,1-dioxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (RS)-3-(benzyloxycarbonylmethyl)-1,2-thiazetidin-2-acetate 1,1-dioxide

There total 1 articles about methyl (RS)-3-(benzyloxycarbonylmethyl)-1,2-thiazetidin-2-acetate 1,1-dioxide 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: 87.0%

bromoacetic acid methyl ester (96-32-2) + benzyl (RS)-1,2-thiazetidin-3-acetate 1,1-dioxide (156977-58-1) → methyl (RS)-3-(benzyloxycarbonylmethyl)-1,2-thiazetidin-2-acetate 1,1-dioxide (757237-19-7)

Guidance literature:

benzyl (RS)-1,2-thiazetidin-3-acetate 1,1-dioxide; With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.0333333h;

bromoacetic acid methyl ester; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

DOI:10.1007/s00706-003-0105-2

Reference yield:

methyl (RS)-3-(benzyloxycarbonylmethyl)-1,2-thiazetidin-2-acetate 1,1-dioxide (757237-19-7) → N-{2-[(RS)-2-(methoxycarbonylmethyl)-1,1-dioxo-1,2-thiazetidin-3-yl]acetyl}-L-phenylalanine methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10 percent Pd/C / tetrahydrofuran / 2 h / 20 °C / 760 Torr

2: 73 percent / N-hydroxysucchinimide; Et₃N; dicyclohexylcarbodiimide / CH₂Cl₂ / -10 - 20 °C

With 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;

DOI:10.1007/s00706-003-0105-2

Reference yield:

methyl (RS)-3-(benzyloxycarbonylmethyl)-1,2-thiazetidin-2-acetate 1,1-dioxide (757237-19-7) → N-{2-[(RS)-2-(methoxycarbonylmethyl)-1,1-dioxo-1,2-thiazetidin-3-yl]acetyl}glycine benzyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10 percent Pd/C / tetrahydrofuran / 2 h / 20 °C / 760 Torr

2: 78 percent / N-hydroxysucchinimide; Et₃N; dicyclohexylcarbodiimide / CH₂Cl₂ / -10 - 20 °C

With 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;

DOI:10.1007/s00706-003-0105-2

upstream raw materials:

bromoacetic acid methyl ester

benzyl (RS)-1,2-thiazetidin-3-acetate 1,1-dioxide