(R)-(-)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE Chemical Properties

Melting point:

45 °C

Boiling point:

396.6±11.0 °C(Predicted)

Density 

1.206±0.06 g/cm3(Predicted)

refractive index 

-103 ° (C=1, EtOH)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform, Ethanol

pka

-2.35±0.40(Predicted)

form 

Solid

color 

Off-White

optical activity

[α]20/D 102°, c = 1 in ethanol

InChI

InChI=1S/C13H15NO3/c1-2-12(15)14-11(9-17-13(14)16)8-10-6-4-3-5-7-10/h3-7,11H,2,8-9H2,1H3/t11-/m1/s1

InChIKey

WHOBYFHKONUTMW-LLVKDONJSA-N

SMILES

O1C[C@@H](CC2=CC=CC=C2)N(C(=O)CC)C1=O

CAS DataBase Reference

131685-53-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

HS Code 

29349990

(R)-(-)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

(R)-(?)-4-Benzyl-3-propionyl-2-oxazolidinone can be used as a building block for the preparation of methyl 3-[(S)-3-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-methyl-3-oxopropyl]benzoate by treating with strong base followed by the addition of methyl 3-bromomethyl benzoate.

Uses

(R)-(-)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE is a oxazolidinone derivative used in the preparation of anisomycin analogues as activators of the JNK/SAPK1 and p38/SAPK2 pathways.

General Description

(R)-(?)-4-Benzyl-3-propionyl-2-oxazolidinone is used as a building block in organic synthesis for the preparation of oxazolidinone derivatives.

Synthesis

Under nitrogen protection, (S)-4-benzyl-2-azolidinone (800 mg, 4.5 mmol) was dissolved in a dry reaction vial of anhydrous tetrahydrofuran (30 mL) and cooled to -78 °C in a dry ice/acetone bath. A hexane solution of 1.6 M n-butyllithium (5.0 mmol, 3.1 mL) was added slowly and dropwise over 3 min. After stirring for 30 min, propionyl chloride (5.0 mmol, 0.43 mL) was added slowly over 3 min. The reaction solution was slowly warmed to room temperature over 14 h. The reaction was subsequently quenched by the addition of saturated ammonium chloride solution (10 mL) and water (30 mL). The aqueous layer was extracted with ethyl acetate (3 x 40 mL), the organic phases were combined and dried over anhydrous magnesium sulfate. The organic phase was concentrated under reduced pressure to afford (R)-(-)-benzyl-3-propionyl-2-oxazolidinone (oil, 1.0 g, 96% yield) with >95% purity by HPLC.1H NMR (500 MHz, CDCl3): δ 7.33 (dd, J1 = 7.4 Hz, J2 = 7.6 Hz, 2H), 7.29 (d, J = 6.9 Hz, 1H) ), 7.21 (d, J = 7.4 Hz, 2H), 4.67 (m, 1H), 4.18 (m, 2H), 3.31 (dd, J1 = 13.3 Hz, J2 = 3.2 Hz, 1H), 2.96 (m, 2H), 2.77 (dd, J1 = 13.3 Hz, J2 = 3.7 Hz, 1H), 1.21 (t, J = 7.4 Hz, 1H). 3H).

References

[1] Chemistry - An Asian Journal, 2011, vol. 6, # 7, p. 1791 - 1799
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 144 - 148
[3] Journal of Organic Chemistry, 2008, vol. 73, # 8, p. 3292 - 3294
[4] Angewandte Chemie - International Edition, 2016, vol. 55, # 13, p. 4252 - 4255
[5] Angew. Chem., 2016, vol. 128, # 13, p. 4324 - 4327,4

(R)-(-)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE(131685-53-5)Related Product Information

• (4S)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone
• (R)-(-)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE
• (R)-4-BENZYL-3-(3-CYCLOPROPYL-PROPIONYL)-OXAZOLIDIN-2-ONE
• (R)-4-BENZYL-3-(4-METHYL-PENTANOYL)-OXAZOLIDIN-2-ONE
• (3S,4R)-4-BENZYL-3-(3-METHYLPENTANOYL)-OXAZOLIDIN-2-ONE
• 3-[(4-METHOXYPHENYL)ACETYL]-(4R)-(PHENYLMETHYL)-2-OXAZOLIDINONE
• 3-(2-PHENYLACETYL)-(4R)-(PHENYLMETHYL)-2-OXAZOLIDINONE
• 3-(4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-4-methyl-hexanoic acid tert-butyl ester
• (R)-3-(3-Methylbutanoyl)-4-benzyloxazolidin-2-one
• (R)-4-BENZYL-3-(3-CYCLOPENTYL-PROPIONYL)-OXAZOLIDIN-2-ONE