(4S)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone Chemical Properties

Melting point:

42-44 °C

alpha 

97 º (c=1, EtOH)

Boiling point:

375.51°C (rough estimate)

Density 

1.1475 (rough estimate)

refractive index 

103 ° (C=1, EtOH)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform, Methanol

form 

Solid

pka

-2.35±0.40(Predicted)

color 

Off-White to Pale Yellow

optical activity

[α]20/D +97°, 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-/m0/s1

InChIKey

WHOBYFHKONUTMW-NSHDSACASA-N

SMILES

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

CAS DataBase Reference

101711-78-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22-43

Safety Statements 

37/39-26-36-36/37

WGK Germany 

3

HS Code 

29349990

MSDS

• Language:English Provider:ACROS

(4S)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone Usage And Synthesis

Chemical Properties

Colourless Solid

Uses

Versatile chiral auxiliary for asymmetric synthesis.

Uses

Intermediate in the preparation of Albaconazole.

Synthesis

Under nitrogen atmosphere, (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 dropwise 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, and 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): δ7.33 (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, 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

(4S)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone(101711-78-8)Related Product Information

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