139149-49-8

Basic information

• Product Name: 3-Oxazolidinecarbonyl chloride, 2-oxo-4-(phenylmethyl)-, (S)-
• CAS NO: 139149-49-8
• Molecular Formula: C11H10ClNO3
• Molecular Weight: 239.658
• Mol File: 139149-49-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3-Oxazolidinecarbonyl chloride, 2-oxo-4-(phenylmethyl)-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Oxazolidinecarbonyl chloride, 2-oxo-4-(phenylmethyl)-, (S)-(139149-49-8)
• EPA Substance Registry System: 3-Oxazolidinecarbonyl chloride, 2-oxo-4-(phenylmethyl)-, (S)-(139149-49-8)

Safety Data

• Hazardous Substances Data: 139149-49-8(Hazardous Substances Data)

Usage

General Description

3-Oxazolidinecarbonyl chloride, 2-oxo-4-(phenylmethyl)-, (S)- is a chemical compound that belongs to the oxazolidinecarbonyl chloride family. It is a chiral molecule, with the (S)-enantiomer being the predominant form. This chemical is commonly used as a reagent in organic synthesis and drug development. Its main applications include the preparation of pharmaceutical intermediates and the synthesis of various organic compounds. It is also known for its use in the production of agrochemicals and fine chemicals. The (S)-enantiomer of 3-Oxazolidinecarbonyl chloride, 2-oxo-4-(phenylmethyl)- is an important building block in organic chemistry and is used in the creation of a wide range of chemical compounds.

Upstream product

• 3182-95-4 L-Phenylalaninol 
• 63-91-2 L-phenylalanine 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 503-38-8 trichloromethyl chloroformate 
• 75-44-5 phosgene 

Downstream Products

• 1239015-87-2 (S)-4-benzyl-3-(1,2-dihydroquinoline-1-carbonyl)oxazolidin-2-one 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 1239015-89-4 (S)-4-benzyl-3-[(1aS,7bR)-1a,2,3,7b-tetrahydrooxireno[2,3-c]quinoline-3-carbonyl]oxazolidine-2-one 
• 1239015-88-3 (S)-4-benzyl-3-[(1aR,7bS)-1a,2,3,7b-tetrahydrooxireno[2,3-c]quinoline-3-carbonyl]oxazolidine-2-one 
• 947612-54-6 C₁₉H₁₃N₂O₅Br 
• 482573-45-5 (2S)-1-{[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-1,2-dihydroquinoline-2-carbonitrile 
• 154656-98-1 [((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-amino]-acetic acid methyl ester 
• 1026190-77-1 C₂₇H₂₅N₃O₇ 

Relevant articles and documents

Radical reaction initiated and stereocontrolled by zinc chloride

The reaction of allyltributyltin with methyl 2-[N-((4S)-4-(1-methylethyl)-2-oxazolidinone-3-carbamoyl)amino]-2-bromoacetate (5 a) was accelerated at -50°C in the presence of AIBN and stopped in the presence of galvinoxyl, indicating that the reaction proceeds through a radical mechanism. The reaction was accelerated dramatically at -78°C in the presence of ZnCl2·OEt2, and the ZnCl2-mediated reaction was stopped in the presence of galvinoxyl. In the presence of 2 equiv ZnCl2·OEt2, the reaction afforded methyl (2R)-2-[N-((4SH-(1-methylethyl)-2-oxazolidinone-3-carbamoyl)amino]-4-pentenoate {6a(R)} with high diastereoselectivity (93:7). Taken together, ZnCl2·OEt2 works as a radical initiator as well as chelating agent.