Benzyl (4S)-4-isopropyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate | CAS No. 158257-41-1

Benzyl (4S)-4-isopropyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate

Basic Information

CAS Number

158257-41-1

Molecular Formula

C14H15NO5

Molecular Weight

277.28 g/mol

AD

Basic Physical Properties

Boiling Point

368°C at 760 mmHg

CC(C)C1C(=O)OC(=O)N1C(=O)OCC2=CC=CC=C2

InChI

InChI=1S/C14H15NO5/c1-9(2)11-12(16)20-14(18)15(11)13(17)19-8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3/t11-/m0/s1

InChIKey

PBXWOGVKYLPBQY-NSHDSACASA-N

LogP

2.3266

Topological Polar Surface Area

72.91000000000001 Ų

Hydrogen Bond Donor/Acceptor

0 / 6

Complexity

400

Safety Information

View Safety Information

Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral
H315 Causes skin irritation
Skin corrosion/irritation
H319 Causes serious eye irritation
Serious eye damage/eye irritation
H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Synonyms & References

English

  • AS-3214
  • Z-VAL-NCA
  • 3-Oxazolidinecarboxylic acid, 4-(1-methylethyl)-2,5-dioxo-, phenylmethyl ester, (4S)-
  • (S)-Benzyl 4-isopropyl-2,5-dioxooxazolidine-3-carboxylate
  • benzyl (4S)-2,5-dioxo-4-(propan-2-yl)-1,3-oxazolidine-3-carboxylate
  • AKOS015911917
  • CS-M3184
  • MFCD00274015
  • J-009486
  • (S)-4-(1-Methylethyl)-2,5-dioxo-3-oxazolidinecarboxylic Acid Phenylmethyl Ester;N-Cbz-L-valine N-Carboxyanhydride
  • SCHEMBL5166676
  • 158257-41-1
  • (S)-3-(Benzyloxycarbonyl)-4-isopropyl-2,5-oxazolidinedione
  • Benzyl (4S)-2,5-dioxo-4-propan-2-yl-1,3-oxazolidine-3-carboxylate
  • AC-31074
  • ZB1796
  • DTXSID30453989
  • (S)-Benzyl4-isopropyl-2,5-dioxooxazolidine-3-carboxylate
  • Z-L-Valine NCA
  • 3-Oxazolidinecarboxylicacid, 4-(1-methylethyl)-2,5-dioxo-, phenylmethyl ester, (4S)-
  • Benzyl (4S)-2,5-dioxo-4-(propan-2-yl)-1,3-oxazolidine-3-carboxylate
  • benzyl (4S)-2,5-dioxo-4-propan-2-yl-1,3-oxazolidine-3-carboxylate
  • N-Cbz-L-valine N-Carboxyanhydride
  • Valine NCA
  • CBZ-Val-NCA
  • Z-Valine, NCA
  • CBZ-L-valine acid NCA
  • Z-L-Valin carboxyanhydride
  • Z-VAINE NCA[FOR VALGANCICLOVIR]
  • (S)-3-(BENZYLOXYCARBONYL)-4-ISOPROPYL
  • benzyl(S)-4-isopropyl-2,5-dioxooxazolidine-3-carboxylate

MDL Number

MFCD00274015

Customs Code

2934999090

FAQ

What are the physical and chemical properties of Benzyl (4S)-4-isopropyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate (CAS: 158257-41-1)?

Benzyl (4S)-4-isopropyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate is a white crystalline solid with a molecular weight of approximately 276.36 g/mol. It has a low solubility in water (less than 0.1 g/100 mL at 20°C) but is more soluble in organic solvents. The compound is highly reactive due to the presence of the oxazolidine ring and the carboxylic acid moiety. It is also prone to hydrolysis and esterification reactions.

How is Benzyl (4S)-4-isopropyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate (CAS: 158257-41-1) typically synthesized?

Benzyl (4S)-4-isopropyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate can be synthesized using a multistep process involving the introduction of the isopropyl group and the oxazolidine skeleton. Common synthesis methods include condensation reactions and ring closing metathesis (RCM) followed by selective oxidation. The reaction is typically carried out under anhydrous conditions using appropriate solvents and catalysts to ensure high yield and selectivity.

What industries use Benzyl (4S)-4-isopropyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate (CAS: 158257-41-1)?

Benzyl (4S)-4-isopropyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate finds applications in various industries, particularly in pharmaceuticals for the synthesis of active pharmaceutical ingredients (APIs) and intermediates. It is also used in the polymer industry as a monomer for the production of functional polymers. Additionally, it has potential applications in the sensor industry for developing gas-sensing materials and in the semiconductor industry for specific chemical processes.

What precautions should be taken when handling Benzyl (4S)-4-isopropyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate (CAS: 158257-41-1)?

When handling Benzyl (4S)-4-isopropyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate, it is essential to wear appropriate personal protective equipment (PPE), including gloves, goggles, and a lab coat. Work should be conducted in a well-ventilated area or fume hood to minimize exposure. Spills should be cleaned up using appropriate absorbent materials, and the area should be thoroughly washed down. Always consult the Safety Data Sheet (SDS) for specific handling and disposal information.

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