(+/-)-methyl 2-{[(2-oxo-1,3-oxazolan-3-yl)sulfonyl]amino}-4-phenylbutanoate

Base Information

• Chemical Name: (+/-)-methyl 2-{[(2-oxo-1,3-oxazolan-3-yl)sulfonyl]amino}-4-phenylbutanoate
• CAS No.: 259794-56-4
• Molecular Formula: C₁₄H₁₈N₂O₆S
• Molecular Weight: 342.373
• Mol file: 259794-56-4.mol

Synonyms:(+/-)-methyl 2-{[(2-oxo-1,3-oxazolan-3-yl)sulfonyl]amino}-4-phenylbutanoate

Chemical Property of (+/-)-methyl 2-{[(2-oxo-1,3-oxazolan-3-yl)sulfonyl]amino}-4-phenylbutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-methyl 2-{[(2-oxo-1,3-oxazolan-3-yl)sulfonyl]amino}-4-phenylbutanoate

There total 1 articles about (+/-)-methyl 2-{[(2-oxo-1,3-oxazolan-3-yl)sulfonyl]amino}-4-phenylbutanoate 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: 57.0%

isocyanate de chlorosulfonyle (1189-71-5) + 2-amino-4-phenylbutyric acid methylester hydrochloride (85808-33-9) + 2-chloro-ethanol (107-07-3) → (+/-)-methyl 2-{[(2-oxo-1,3-oxazolan-3-yl)sulfonyl]amino}-4-phenylbutanoate (259794-56-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 12h;

DOI:10.1002/(SICI)1522-2675(19991215)82:12<2432::AID-HLCA2432>3.0.CO;2-H

Reference yield: 64.0%

3-amino-2,2-dimethylpropionic acid tert-butyl ester (259794-53-1) + (+/-)-methyl 2-{[(2-oxo-1,3-oxazolan-3-yl)sulfonyl]amino}-4-phenylbutanoate (259794-56-4) → (+/-)-methyl 2-[({[2-(tert-butoxycarbonyl)-2,2-dimethylethyl]amino}sulfonyl)amino]-4-phenylbutanoate (259794-60-0)

Guidance literature:

With triethylamine; In acetonitrile; for 12h; Heating;

DOI:10.1002/(SICI)1522-2675(19991215)82:12<2432::AID-HLCA2432>3.0.CO;2-H

Reference yield:

(+/-)-methyl 2-{[(2-oxo-1,3-oxazolan-3-yl)sulfonyl]amino}-4-phenylbutanoate (259794-56-4) → (+/-)-2,2-dimethyl-3-[4-(2-phenylethyl)-1,1,3-trioxo-1λ6,2,5-thiadiazolan-2-yl]propanoic acid

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / Et₃N / acetonitrile / 12 h / Heating

2: 65 percent / NaH / tetrahydrofuran / 7 h / Heating

3: 86 percent / TFA / 3 h / 20 °C

With sodium hydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; acetonitrile; 1: Substitution / 2: Cyclization / 3: Hydrolysis;

DOI:10.1002/(SICI)1522-2675(19991215)82:12<2432::AID-HLCA2432>3.0.CO;2-H

upstream raw materials:

isocyanate de chlorosulfonyle

2-amino-4-phenylbutyric acid methylester hydrochloride

2-chloro-ethanol

Downstream raw materials:

(+/-)-methyl 2-[({[2-(tert-butoxycarbonyl)-2,2-dimethylethyl]amino}sulfonyl)amino]-4-phenylbutanoate

(+/-)-tert-butyl 2,2-dimethyl-3-[4-(2-phenylethyl)-1,1,3-trioxo-1λ⁶,2,5-thiadiazolan-2-yl]propanoate