(S)-(-)-4-(4-hydroxybenzyl)-2-oxazolidinone

Base Information

• Chemical Name: (S)-(-)-4-(4-hydroxybenzyl)-2-oxazolidinone
• CAS No.: 187332-12-3
• Molecular Formula: C10H11 N O3
• Molecular Weight: 193.202
• DSSTox Substance ID: DTXSID40472141
• Nikkaji Number: J820.827A
• Wikidata: Q82300930
• Mol file: 187332-12-3.mol

Synonyms:(S)-(-)-4-(4-hydroxybenzyl)-2-oxazolidinone;187332-12-3;(S)-4-(4-Hydroxybenzyl)oxazolidin-2-one;(4S)-4-[(4-hydroxyphenyl)methyl]-1,3-oxazolidin-2-one;SCHEMBL2477224;DTXSID40472141;ZPLCXHWYPWVJDL-QMMMGPOBSA-N

Chemical Property of (S)-(-)-4-(4-hydroxybenzyl)-2-oxazolidinone

Chemical Property:

• PSA: 58.56000
• LogP: 1.37190
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 193.07389321
• Heavy Atom Count: 14
• Complexity: 211

Purity/Quality:

98% ^*data from raw suppliers

(S)-(-)-4-(4-HYDROXYBENZYL)-2-OXAZOLIDINONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(NC(=O)O1)CC2=CC=C(C=C2)O
• Isomeric SMILES: C1[C@@H](NC(=O)O1)CC2=CC=C(C=C2)O

Technology Process of (S)-(-)-4-(4-hydroxybenzyl)-2-oxazolidinone

There total 16 articles about (S)-(-)-4-(4-hydroxybenzyl)-2-oxazolidinone 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: 94.0%

(S)-4-(4-(benzyloxy)benzyl)oxazolidin-2-one (170438-03-6) → (4S)-4-(4-hydroxybenzyl)-1,3-oxazolidin-2-one (187332-12-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2017.04.026

Reference yield: 58.0%

4-(trifluoromethoxy)benzonitrile (332-25-2) + 4-((S)-2-amino-3-hydroxy-propyl)-phenol hydrochloride (40829-04-7) → (4S)-4-(4-hydroxybenzyl)-1,3-oxazolidin-2-one (187332-12-3)

Guidance literature:

With 3,7-di([1,1′-biphenyl]-4-yl)-10-(naphthalen-1-yl)-10H-phenoxazine; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 24h; Reagent/catalyst; Inert atmosphere; Irradiation; Sealed tube;

DOI:10.1002/chem.201804603

Reference yield: 50.0%

(S)-2-amino-N-ethoxycarbonyl-3-(4-hydroxyphenyl)-propanol (385842-97-7) → (4S)-4-(4-hydroxybenzyl)-1,3-oxazolidin-2-one (187332-12-3)

Guidance literature:

With potassium carbonate; In toluene; for 4h; Heating;

DOI:10.1016/S0040-4020(01)00769-4

upstream raw materials:

N-[(phenylmethoxy)carbonyl]-L-tyrosine

(S)-4-(4-(benzyloxy)benzyl)oxazolidin-2-one

(S)-2-amino-N-ethoxycarbonyl-3-(4-hydroxyphenyl)-propanol

4-[(2S)-2-amino-3-hydroxypropyl]phenol

Downstream raw materials:

3-phenylpropanoic acid methyl ester

3-Phenylpropionic acid

(S)-4-(4-(benzyloxy)benzyl)oxazolidin-2-one

C₂₂H₂₅NO₄