(r)-Tert-butyl 4-(2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate

Base Information

• Chemical Name: (r)-Tert-butyl 4-(2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate
• CAS No.: 154590-62-2
• Molecular Formula: C19H26FN3O5
• Molecular Weight: 395.431
• ChEMBL ID: CHEMBL596912
• DSSTox Substance ID: DTXSID20583305
• Wikidata: Q82474853
• Mol file: 154590-62-2.mol

Synonyms:154590-62-2;(r)-tert-butyl 4-(2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate;tert-butyl 4-[2-fluoro-4-[(5R)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]piperazine-1-carboxylate;1-Piperazinecarboxylic acid,4-[2-fluoro-4-[(5R)-5-(hydroxymethyl)-2-oxo-3-oxazolidinyl]phenyl]-,1,1-dimethylethyl ester;MOYRUYYEQYIFJI-CQSZACIVSA-N;tert-butyl 4-{2-fluoro-4-[(5r)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}piperazine-1-carboxylate;CHEMBL596912;SCHEMBL6111262;C19H26FN3O5;DTXSID20583305;AKOS015924496;AKOS015995194;3-(3-Fluoro-4-(4-t-butoxycarbonylpiperazin-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one;5(R)-hydroxymethyl-3-(3-fluoro-4-(4-t-butoxycarbonylpiperazin-1-yl)phenyl)oxazolidin-2-one;3-(4-(4-t-Butoxycarbonyl-piperazin-1-yl)-3-fluorophenyl)-5(R)-hydroxymethyloxazolidin-2-one

Chemical Property of (r)-Tert-butyl 4-(2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate

Chemical Property:

• Melting Point: 130-131 °C
• Boiling Point: 552.2±50.0 °C(Predicted)
• PKA: 14.05±0.10(Predicted)
• PSA: 82.55000
• Density: 1.297±0.06 g/cm3(Predicted)
• LogP: 2.26820
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 395.18564910
• Heavy Atom Count: 28
• Complexity: 576

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCN(CC1)C2=C(C=C(C=C2)N3CC(OC3=O)CO)F
• Isomeric SMILES: CC(C)(C)OC(=O)N1CCN(CC1)C2=C(C=C(C=C2)N3C[C@@H](OC3=O)CO)F

Technology Process of (r)-Tert-butyl 4-(2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate

There total 8 articles about (r)-Tert-butyl 4-(2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-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: 71.0%

tert-butyl 4-(4-(benzyloxycarbonyl)-2-fluorophenyl)piperazine-1-carboxylate (154590-36-0) + (R)-glycidyl butyrate (60456-26-0) → (R)-tert-butyl-4-(2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate (154590-62-2)

Guidance literature:

tert-butyl 4-(4-(benzyloxycarbonyl)-2-fluorophenyl)piperazine-1-carboxylate; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.333333h; Inert atmosphere;

(R)-glycidyl butyrate; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2009.10.018

Reference yield:

tert-butyl 4-(4-(benzyloxycarbonyl)-2-fluorophenyl)piperazine-1-carboxylate (154590-36-0) → (R)-tert-butyl-4-(2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate (154590-62-2)

Guidance literature:

tert-butyl 4-(4-(benzyloxycarbonyl)-2-fluorophenyl)piperazine-1-carboxylate; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

With (R)-glycidyl butyrate;

Reference yield:

tert-butyl 4-(4-amino-2-fluorophenyl)piperazine-1-carboxylate (154590-35-9) → (R)-tert-butyl-4-(2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate (154590-62-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaHCO₃ / tetrahydrofuran

2.1: n-BuLi / tetrahydrofuran / 1.5 h / -78 °C

2.2: tetrahydrofuran

With n-butyllithium; sodium hydrogencarbonate; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2005.06.063

upstream raw materials:

tert-butyl 4-(4-(benzyloxycarbonyl)-2-fluorophenyl)piperazine-1-carboxylate

(R)-glycidyl butyrate

tert-butyl 4-(4-amino-2-fluorophenyl)piperazine-1-carboxylate

4-(2-fluoro-4-nitrophenyl)-piperazine-1-carboxylic acid tert butyl ester

Downstream raw materials:

tert-butyl 4-(2-fluoro-4-{(5R)-2-oxo-5-[(pyrazin-2-yloxy)methyl]-1,3-oxazolidin-3-yl}phenyl)piperazine-1-carboxylate

tert-butyl 4-(4-{(5R)-5-[(acetyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)piperazine-1-carboxylate