Contact us: +91 9550333722 040 - 40102781
Structured search
India
Choose your country
Different countries will display different contents
Try our best to find the right business for you.
My chemicalbook

Welcome back!

HomeProduct name list(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE

Synonym(s):(4R,5S)-4-Methyl-5-phenyl-2-oxazolidinone

  • CAS NO.:77943-39-6
  • Empirical Formula: C10H11NO2
  • Molecular Weight: 177.2
  • MDL number: MFCD00010845
  • EINECS: 660-040-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-05-25 10:25:51
(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE Structural

What is (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE?

Chemical properties

white to light yellow crystal powde

The Uses of (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE

(4R,5S)-4-Methyl-5-phenyloxazolidinone is used as effective chiral auxiliary for conjugate addition asymmetric synthesis of (-)-aplysillamide B.

The Uses of (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE

Evan′s chiral auxiliary (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone reacts with carboxylic acids to produce corresponding acyl derivatives in the presence of a diisopropylcarbodiimide reagent. It can also employed in the preparation of N-sulfinyloxazolidinone reagent (chiral sulfinyl transfer reagent), which reacts with nucleophiles such as Grignard reagents, enolates, and metalated amides to produce the chiral sulfoxides, sulfinate esters, and sulfonamides.

What are the applications of Application

(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone is a chiral auxiliary in condensation reactions with acyl halides and carboxylic acids.

Preparation

To a solution of (1S,2R)-norephedrine (40 g, 0.26 mol) in toluene (400 mL) was added diethyl carbonate (37 mL, 0.32 mol). The mixture was heated to reflux (under Ar) while 40 mL of solvent was removed through the use of a Dean–Stark apparatus. The mixture was allowed to cool for 20 min, and then sodium methoxide (1 g) was added. Upon reheating, an EtOH/toluene azeotropic mixture was removed at 75–77 °C. After 3 h, the reaction was complete and the temperature of the mixture had increased to 125 °C. The mixture was left to stand at room temperature for 16 h, whereupon (4R,5S)-4-methyl-5-phenyloxazolidin-2-one (40.6 g) crystallized and could be collected. The solvent was removed from the filtrate in vacuo and the residue was redissolved in EtOAc (250 mL). This solution was washed with brine (50 mL) and a precipitate was removed by filtration. The solvent was then removed in vacuo and toluene (50 mL) was added to the residue. Removal of the toluene by distillation yielded oily crystals of the oxazolidinone, which were washed with Et2O to afford 4.5 g (total 45 g, 97%).

Preparation

A mechanically stirred mixture of (1S,2R)-norephedrine 710 (151 g, 1.00 mol) ([α]589 =+ 33.4 (c= 7, water)), as the hydrochloride salt, diphenyl carbonate (236 g, 1.10 mol), and anhydrous potassium carbonate (152 g, 1.10 mol) was heated at 110 °C for 4–6 h. The resultant mixture was then cooled to <60 °C. Excess diphenyl carbonate was hydrolyzed by adding methanol (600 mL) and heating the mixture under reflux for 0.5 h. Sufficient water (400–600 mL) was then added to dissolve the potassium carbonate. Methanol was removed in vacuo. The product and phenol were extracted into dichloromethane (3 × 1 L). The combined extracts were washed with 2 m aqueous sodium hydroxide (3 × 1 L) to remove the phenol, 1 m aqueous hydrochloric acid (1 × 1 L), and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give 195 g (110% mass balance) of a light-yellow solid. Recrystallization from toluene (600 mL) afforded 145–165 g (82–93%) of oxazolidinone 711 as a white crystalline solid.
the preparation of (4R,5S)-4-Methyl-5-phenyl-2-oxazolidinone

Definition

ChEBI: (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone is a member of benzenes.

Synthesis Reference(s)

Tetrahedron Letters, 40, p. 6059, 1999 DOI: 10.1016/S0040-4039(99)01256-3

Properties of (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE

Melting point: 121-123 °C(lit.)
Boiling point: 309.12°C (rough estimate)
Density  1.1607 (rough estimate)
refractive index  1.5168 (estimate)
storage temp.  Sealed in dry,Room Temperature
solubility  Chloroform (Slightly), Ethyl Acetate (Slightly)
form  Liquid
pka 12.35±0.60(Predicted)
color  Clear colorless to yellow-brown, may darken in storage
optical activity [α]18/D +168°, c = 2 in chloroform
BRN  1211705
InChI InChI=1S/C10H11NO2/c1-7-9(13-10(12)11-7)8-5-3-2-4-6-8/h2-7,9H,1H3,(H,11,12)/t7-,9-/m1/s1
CAS DataBase Reference 77943-39-6(CAS DataBase Reference)

Safety information for (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE

InChIKey PPIBJOQGAJBQDF-VXNVDRBHSA-N
SMILES O1[C@@H](C2=CC=CC=C2)[C@@H](C)NC1=O

Related products of tetrahydrofuran

You may like

Statement: All products displayed on this website are only used for non medical purposes such as industrial applications or scientific research, and cannot be used for clinical diagnosis or treatment of humans or animals. They are not medicinal or edible.