2-Oxazolidinone, 3-[(2S,4R)-4-bromo-2-(1-methylethyl)-1-oxo-4-[(2S,4S)-tetrahydro-4-(1-methylethyl)-5-oxo-2-furanyl]butyl]-4-(phenylmethyl)-, (4S)-

Base Information

• Chemical Name: 2-Oxazolidinone, 3-[(2S,4R)-4-bromo-2-(1-methylethyl)-1-oxo-4-[(2S,4S)-tetrahydro-4-(1-methylethyl)-5-oxo-2-furanyl]butyl]-4-(phenylmethyl)-, (4S)-
• CAS No.: 173154-00-2
• Molecular Formula: C24H32BrNO5
• Molecular Weight: 494.426
• European Community (EC) Number: 605-664-0
• DSSTox Substance ID: DTXSID101100842
• Mol file: 173154-00-2.mol

Synonyms:173154-00-2;2-Oxazolidinone, 3-[(2S,4R)-4-bromo-2-(1-methylethyl)-1-oxo-4-[(2S,4S)-tetrahydro-4-(1-methylethyl)-5-oxo-2-furanyl]butyl]-4-(phenylmethyl)-, (4S)-;3(S)-isopropyl-5(S)-{1(R)-bromo-4-methyl-3(S)-[(4(S)-benzyl-oxazolidin-2-on-3-yl)-carbonyl]-pentyl)-tetrahydrofuran-2-one;3(S)-isopropyl-5(S)-{1(R)-bromo-4-methyl-3(S)-[(4(S)-benzyl-oxazolidin-2-on-3-yl)-carbonyl]-pentyl}-tetrahydrofuran-2-one;SCHEMBL6045401;DTXSID101100842;(4S)-3-[(2S,4R)-4-Bromo-2-(1-methylethyl)-1-oxo-4-[(2S,4S)-tetrahydro-4-(1-methylethyl)-5-oxo-2-furanyl]butyl]-4-(phenylmethyl)-2-oxazolidinone;(4S)-4-Benzyl-3-[(2S,4R)-4-bromo-2-isopropyl-4-[(2S,4S)-4-isopropyl-5-oxo-tetrahydrofuran-2-yl]butanoyl]oxazolidin-2-one;(4S)-4-benzyl-3-[(2S,4R)-4-bromo-4-[(2S,4S)-5-oxo-4-propan-2-yloxolan-2-yl]-2-propan-2-ylbutanoyl]-1,3-oxazolidin-2-one;(S)-4-Benzyl-3-((S)2-((R) -2-BroMo-2((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-Methyl-butyr;3(S)-isopropyl-5(S)-{1(R)-bromo-4-methyl-3(S)-[(4(S)-benzyloxazolidin-2-on-3-yl)-carbonyl]-pentyl}-tetrahydrofuran-2-one

Chemical Property of 2-Oxazolidinone, 3-[(2S,4R)-4-bromo-2-(1-methylethyl)-1-oxo-4-[(2S,4S)-tetrahydro-4-(1-methylethyl)-5-oxo-2-furanyl]butyl]-4-(phenylmethyl)-, (4S)-

Chemical Property:

• Vapor Pressure: 1.35E-15mmHg at 25°C
• Melting Point: 91.2 °C
• Boiling Point: 626.2°C at 760 mmHg
• PKA: -2.37±0.40(Predicted)
• Flash Point: 332.5°C
• PSA: 72.91000
• Density: 1.315g/cm³
• LogP: 4.52790
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 493.14639
• Heavy Atom Count: 31
• Complexity: 660

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1CC(OC1=O)C(CC(C(C)C)C(=O)N2C(COC2=O)CC3=CC=CC=C3)Br
• Isomeric SMILES: CC(C)[C@@H]1C[C@H](OC1=O)[C@@H](C[C@@H](C(C)C)C(=O)N2[C@H](COC2=O)CC3=CC=CC=C3)Br

Technology Process of 2-Oxazolidinone, 3-[(2S,4R)-4-bromo-2-(1-methylethyl)-1-oxo-4-[(2S,4S)-tetrahydro-4-(1-methylethyl)-5-oxo-2-furanyl]butyl]-4-(phenylmethyl)-, (4S)-

There total 6 articles about 2-Oxazolidinone, 3-[(2S,4R)-4-bromo-2-(1-methylethyl)-1-oxo-4-[(2S,4S)-tetrahydro-4-(1-methylethyl)-5-oxo-2-furanyl]butyl]-4-(phenylmethyl)-, (4S)- 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: 82.0%

(4S,4'S)-3,3'-((2S,2'S)-2,2'-((2S,3S)-oxirane-2,3-diylbis-(methylene))bis(3-methylbutanoyl))bis(4-benzyloxazolidin-2-one) → (S)-4-benzyl-3-((2S,4R)-4-bromo-2-isopropyl-4-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-butanoyl)oxazolidin-2-one (173154-00-2)

Guidance literature:

With magnesium(II) perchlorate; lithium bromide; In tetrahydrofuran; at 80 ℃; for 4h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

DOI:10.1021/acs.oprd.5b00009

Reference yield:

(2S,4E,7S)-2,7-bis(1-methylethyl)-1,8-bis[(4S)-2-oxo-4-(phenylmethyl)oxazolidin-3-yl]oct-4-ene-1,8-dione → (S)-4-benzyl-3-((2S,4R)-4-bromo-2-isopropyl-4-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-butanoyl)oxazolidin-2-one (173154-00-2)

Guidance literature:

With N-Bromosuccinimide; water; In tetrahydrofuran; at 20 ℃; for 2h;

Reference yield:

isopentanoyl chloride (108-12-3) → (S)-4-benzyl-3-((2S,4R)-4-bromo-2-isopropyl-4-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-butanoyl)oxazolidin-2-one (173154-00-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran / 1.5 h / -30 - -25 °C / Inert atmosphere

1.2: 1.5 h / -25 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -50 °C / Inert atmosphere; Large scale

2.2: 2 h / -50 °C / Inert atmosphere; Large scale

2.3: 3.5 h / -50 - 10 °C / Inert atmosphere; Large scale

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h / 0 °C / Large scale

4.1: lithium bromide; magnesium(II) perchlorate / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere

With n-butyllithium; magnesium(II) perchlorate; 3-chloro-benzenecarboperoxoic acid; lithium bromide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/acs.oprd.5b00009

upstream raw materials:

(S)-4-Benzyl-2-oxazolidinone

isopentanoyl chloride

(S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one

Downstream raw materials:

(S)-3-((2S,4S)-4-azido-2-isopropyl-4-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)butanoyl)-4-benzyloxazolidin-2-one

(3S,5S)-tert-butyl-3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-2-oxopyrrolidine-1-carboxylate

(3S,5S)-3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)pyrrolidin-2-one

(S)-4-Benzyl-2-oxazolidinone