(S)-BENZYL 4-(N-METHOXY-N-METHYLCARBAMOYL)-2,2-DIMETHYLOXAZOLIDINE-3-CARBOXYLATE

Base Information

• Chemical Name: (S)-BENZYL 4-(N-METHOXY-N-METHYLCARBAMOYL)-2,2-DIMETHYLOXAZOLIDINE-3-CARBOXYLATE
• CAS No.: 412917-35-2
• Molecular Formula: C16H22N2O5
• Molecular Weight: 322.361
• Mol file: 412917-35-2.mol

Synonyms:(S)-BENZYL 4-(N-METHOXY-N-METHYLCARBAMOYL)-2,2-DIMETHYLOXAZOLIDINE-3-CARBOXYLATE

Chemical Property of (S)-BENZYL 4-(N-METHOXY-N-METHYLCARBAMOYL)-2,2-DIMETHYLOXAZOLIDINE-3-CARBOXYLATE

Chemical Property:

• PSA: 68.31000
• LogP: 1.71780

Purity/Quality:

(S)-BENZYL-4-(N-METHOXY-N-METHYLCARBAMOYL)-2,2-DIMETHYLOXAZOLIDINE-3-CARBOXYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-BENZYL 4-(N-METHOXY-N-METHYLCARBAMOYL)-2,2-DIMETHYLOXAZOLIDINE-3-CARBOXYLATE

There total 3 articles about (S)-BENZYL 4-(N-METHOXY-N-METHYLCARBAMOYL)-2,2-DIMETHYLOXAZOLIDINE-3-CARBOXYLATE 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: 93.0%

2,2-dimethoxy-propane (77-76-9) + benzyl N-[(1S)-1-(hydroxymethyl)-2-[methoxy(methyl)amino]-2-oxo-ethyl]carbamate (684270-34-6) → benzyl (4S)-{[methoxy(methyl)amino]carbonyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (412917-35-2)

Guidance literature:

With boron trifluoride diethyl etherate; In acetone;

DOI:10.1016/S0040-4039(99)01613-5

Reference yield:

N-(benzyloxycarbonyl)-L-serine (1145-80-8) → benzyl (4S)-{[methoxy(methyl)amino]carbonyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (412917-35-2)

Guidance literature:

Multi-step reaction with 2 steps

1: N-methylmorpholine; 1-(3-dimethylaminopopyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 1 h / -15 °C

2: 29.6 percent / BF₃*OEt₂ / acetone / 2 h

With 4-methyl-morpholine; boron trifluoride diethyl etherate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; acetone;

DOI:10.1021/jo010865a

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → benzyl (4S)-{[methoxy(methyl)amino]carbonyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (412917-35-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydrogencarbonate / water; tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

2.1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1.5 h / Inert atmosphere

2.2: 4.5 h / Inert atmosphere

With 4-methyl-morpholine; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/anie.201800169

upstream raw materials:

2,2-dimethoxy-propane

benzyl N-[(1S)-1-(hydroxymethyl)-2-[methoxy(methyl)amino]-2-oxo-ethyl]carbamate

N-(benzyloxycarbonyl)-L-serine

benzyl chloroformate