(S)-Benzyl 4-isopropyl-2,5-dioxooxazolidine-3-carboxylate

Base Information

• Chemical Name: (S)-Benzyl 4-isopropyl-2,5-dioxooxazolidine-3-carboxylate
• CAS No.: 158257-41-1
• Molecular Formula: C₁₄H₁₅NO₅
• Molecular Weight: 277.277
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID30453989
• Wikidata: Q72442006
• Mol file: 158257-41-1.mol

Synonyms:158257-41-1;(S)-Benzyl 4-isopropyl-2,5-dioxooxazolidine-3-carboxylate;(S)-3-(Benzyloxycarbonyl)-4-isopropyl-2,5-oxazolidinedione;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;Z-VAL-NCA;(S)-3-(Benzyloxycarbonyl)-4-isopropyl-2,5-oxazolid;SCHEMBL5166676;DTXSID30453989;CS-M3184;MFCD00274015;ZB1796;AKOS015911917;AS-3214;AC-31074;J-009486;(S)-Benzyl4-isopropyl-2,5-dioxooxazolidine-3-carboxylate;3-Oxazolidinecarboxylic acid, 4-(1-methylethyl)-2,5-dioxo-, phenylmethyl ester, (4S)-;(S)-4-(1-Methylethyl)-2,5-dioxo-3-oxazolidinecarboxylic Acid Phenylmethyl Ester;N-Cbz-L-valine N-Carboxyanhydride

Chemical Property of (S)-Benzyl 4-isopropyl-2,5-dioxooxazolidine-3-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.553
• Boiling Point: 367.988 °C at 760 mmHg
• PKA: -3.15±0.40(Predicted)
• Flash Point: 176.353 °C
• PSA: 72.91000
• Density: 1.294 g/cm³
• LogP: 2.26450
• Solubility.: Chloroform, Tetrahydrofuran
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 277.09502258
• Heavy Atom Count: 20
• Complexity: 400

Purity/Quality:

98%, ^*data from raw suppliers

(S)-3-(Benzyloxycarbonyl)-4-isopropyl-2,5-oxazolidinedione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1C(=O)OC(=O)N1C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: CC(C)[C@H]1C(=O)OC(=O)N1C(=O)OCC2=CC=CC=C2

Technology Process of (S)-Benzyl 4-isopropyl-2,5-dioxooxazolidine-3-carboxylate

There total 2 articles about (S)-Benzyl 4-isopropyl-2,5-dioxooxazolidine-3-carboxylate 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: 88.3%

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) + 1,1'-carbonyldiimidazole (530-62-1) → (S)-3-benzyloxycarbonyl-4-isopropyl-2,5-oxazolidinedione (178614-85-2,158257-41-1)

Guidance literature:

(S)-N-(benzyloxycarbonyl)valine; With dmap; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Inert atmosphere; Large scale;

1,1'-carbonyldiimidazole; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 - 25 ℃; for 6h; Reagent/catalyst; Temperature; Solvent; Large scale;

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) + 4-isopropyl-2,5-oxazolidinedione (2816-12-8,24601-74-9) → 4-isopropyl-2,5-dioxo-oxazolidine-3-carboxylic acid benzyl ester (394210-42-5,178614-85-2,158257-41-1)

Guidance literature:

With 4-methyl-morpholine; In tetrahydrofuran; at -25 - 20 ℃;

DOI:10.1021/ja011936q

upstream raw materials:

(S)-N-(benzyloxycarbonyl)valine

1,1'-carbonyldiimidazole

benzyl chloroformate

4-isopropyl-2,5-oxazolidinedione

Refernces

• 1、 Hang,Tian,Tang,Deng. "Asymmetric synthesis of α-amino acids via cinchona alkaloid-catalyzed kinetic resolution of urethane-protected α-amino acid N-carboxyanhydrides". . p. 12696 - 12697. Retrieved 2007/10/03.