(S)-tert-butyl 2-oxo-5-phenylmorpholine-4-carboxylate

Base Information

• Chemical Name: (S)-tert-butyl 2-oxo-5-phenylmorpholine-4-carboxylate
• CAS No.: 220077-24-7
• Molecular Formula: C₁₅H₁₉NO₄
• Molecular Weight: 277.32
• Hs Code.: 2934999090
• European Community (EC) Number: 812-776-5
• DSSTox Substance ID: DTXSID00449354
• Nikkaji Number: J1.027.960G
• Wikidata: Q72510514
• Mol file: 220077-24-7.mol

Synonyms:220077-24-7;(S)-tert-butyl 2-oxo-5-phenylmorpholine-4-carboxylate;(5S)-N-(tert-butoxycarbonyl)-3,4,5,6-tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one;(S)-4-BOC-5-Phenylmorpholin-2-one;TERT-BUTYL (5S)-2-OXO-5-PHENYLMORPHOLINE-4-CARBOXYLATE;AC-4309;DTXSID00449354;AKOS015901964;BS-27707;tert-butyl (S)-2-oxo-5-phenylmorpholine-4-carboxylate;(5S)-4-(tert-Butyloxycarbonyl)-5-phenylmorpholine-2-one;(5S)-N-tert-Butyloxycarbonyl-3,4,5,6-tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one

Chemical Property of (S)-tert-butyl 2-oxo-5-phenylmorpholine-4-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.53
• Boiling Point: 435.361 °C at 760 mmHg
• Flash Point: 217.099 °C
• PSA: 55.84000
• Density: 1.173 g/cm³
• LogP: 2.45950
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 277.13140809
• Heavy Atom Count: 20
• Complexity: 369

Purity/Quality:

99.3% ^*data from raw suppliers

(5S)-N-tert-Butyloxycarbonyl-3,4,5,6-tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(=O)OCC1C2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N1CC(=O)OC[C@@H]1C2=CC=CC=C2

Technology Process of (S)-tert-butyl 2-oxo-5-phenylmorpholine-4-carboxylate

There total 4 articles about (S)-tert-butyl 2-oxo-5-phenylmorpholine-4-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: 78.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-5-phenyl-3,4,5,6-tetrahydro-2H-1,4-oxazin-2-one (121269-45-2,134872-85-8) → (5R)-4-(tert-butyloxycarbonyl)-5-phenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (119878-90-9,220077-24-7)

Guidance literature:

With triethylamine; In ethyl acetate; for 6h; Ambient temperature;

DOI:10.1021/jo00277a032

Reference yield: 58.0%

di-tert-butyl dicarbonate (24424-99-5) + (5S)-5-phenylmorpholin-2-one (144896-92-4,134872-85-8) → (S)-2,3,5,6-tetrahydro-5-phenyl-N-(tert-butyloxycarbonyl)-4H-1,4-oxazine-2-one (220077-24-7)

Guidance literature:

With triethylamine; In ethyl acetate; at 20 ℃; for 6h;

DOI:10.1016/j.tet.2021.132035

Reference yield:

D-2-phenylglycinol (56613-80-0) → (5R)-4-(tert-butyloxycarbonyl)-5-phenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (119878-90-9,220077-24-7)

Guidance literature:

Multi-step reaction with 2 steps

1: diisopropylethylamine / acetonitrile

2: ethyl acetate / 16 h / 25 °C

With N-ethyl-N,N-diisopropylamine; In ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4039(00)82269-8

upstream raw materials:

di-tert-butyl dicarbonate

(R)-5-phenyl-3,4,5,6-tetrahydro-2H-1,4-oxazin-2-one

D-2-phenylglycinol

(2S)-2-phenylglycinol

Downstream raw materials:

(E)-3-(3-(diethylphosphono)prop-2-en-1-yl)-4-(tert-butoxycarbonyl)-5-phenyl-2H-1,4-oxazin-2-one

(3R,5R)-3-Benzyloxycarbonylmethyl-2-oxo-5-phenyl-morpholine-4-carboxylic acid tert-butyl ester

(3S,5R)-3-Benzyloxycarbonylmethyl-2-oxo-5-phenyl-morpholine-4-carboxylic acid tert-butyl ester

(3S,5S)-3-allyl-5-phenylmorpholin-2-one