2-Oxazolidinone, 4-(phenylmethyl)-

Base Information

• Chemical Name: 2-Oxazolidinone, 4-(phenylmethyl)-
• CAS No.: 40217-17-2
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.203
• Mol file: 40217-17-2.mol

Synonyms:

Chemical Property of 2-Oxazolidinone, 4-(phenylmethyl)-

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Oxazolidinone, 4-(phenylmethyl)-

There total 94 articles about 2-Oxazolidinone, 4-(phenylmethyl)- 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: 100.0%

N-tert-butoxycarbonyl-D-Phenylalaninol (106454-69-7) → (R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7)

Guidance literature:

With thionyl chloride; In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1016/S0040-4020(96)01077-0

Reference yield: 97.0%

carbon dioxide (124-38-9,18923-20-1) + (R)-2-amino-3-phenylpropanol (5267-64-1) → (R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7)

Guidance literature:

With triethylamine; chlorophosphoric acid diphenyl ester; In acetonitrile; at -40 - 25 ℃;

DOI:10.1021/jo100268n

Reference yield: 96.0%

(R)-3-((2R,4R)-2-Azido-4-methyl-hexanoyl)-4-benzyl-oxazolidin-2-one (221293-03-4) → (R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7) + (2R,4R)-2-Azido-4-methyl-hexanoic acid (221293-04-5)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 0.5h;

upstream raw materials:

4-methoxy-1,3-oxazolidin-2-one

benzylmagnesium chloride

(S)-4-Benzyl-3-[(2S,3R,4R,6S,7R,8S,10R)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6,8-dimethoxy-2-(4-methoxy-benzyloxy)-4,10-dimethyl-11-triisopropylsilanyloxy-undecanoyl]-oxazolidin-2-one

2-benzylaziridine

Downstream raw materials:

(S)-4-Benzyl-3-((1S,2R,4R)-2-methoxy-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carbonyl)-oxazolidin-2-one

(R)-4-Benzyl-3-((1S,2R,4R)-2-methoxy-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carbonyl)-oxazolidin-2-one

(R)-4-(phenylmethyl)-2-oxazolidinone

(S)-4-Benzyl-2-oxazolidinone

Refernces

Stereochemical selectivity of methanandamides for the CB1 and CB2 cannabinoid receptors and their metabolic stability

10.1016/S0968-0896(01)00088-8

The research aimed to evaluate the stereoselectivity of chiral analogues of the endogenous cannabinoid receptor ligand, arachidonylethanolamide (anandamide), in binding to CB1 and CB2 cannabinoid receptors and their metabolic stability. The study synthesized several chiral anandamide analogues with methyl groups introduced at the 2,1 and 20 positions using asymmetric synthesis. The researchers found that the introduction of a single 2-methyl group increased affinity for CB1, but only modestly improved metabolic stability. However, the 2,1-dimethyl analogues exhibited high enantio- and diastereoselectivity, with (R)-N-(1-methyl-2-hydroxyethyl)-2-(R)-methyl-arachidonamide (4) showing the highest CB1 receptor affinity. The study concluded that a partial CB1 receptor site model could be proposed, featuring two hydrophobic pockets capable of accommodating 1- and 2-methyl groups. Key chemicals used in the process included arachidonic acid, various amino alcohols, and chiral auxiliaries like 4-benzyl-2-oxazolidinone, along with reagents such as oxalyl chloride, lithium hydroxide, and phenylmethanesulfonyl fluoride (PMSF) for enzyme inhibition during binding assays.

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