220077-24-7

Basic information

• Product Name: (5S)-N-(tert-Butoxycarbonyl)-3,4,5,6-tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one
• Synonyms: (5S)-N-(TERT-BUTOXYCARBONYL)-3,4,5,6-TETRAHYDRO-5-PHENYL-4(H)-1,4-OXAZIN-2-ONE;(5S)-N-TERT BUTYLOXYCARBONYL-3,4,5,6-TETRAHYDRO-5-PHENYL-4(H)-1,4-OXAZIN-2-ONE;(S)-tert-butyl 2-oxo-5-phenylmorpholine-4-carboxylate
• CAS NO: 220077-24-7
• Molecular Formula: C15H19NO4
• Molecular Weight: 277.32
• Mol File: 220077-24-7.mol

Chemical Properties

• Boiling Point: 435.361 °C at 760 mmHg
• Flash Point: 217.099 °C
• Appearance: /
• Density: 1.173 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.53
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (5S)-N-(tert-Butoxycarbonyl)-3,4,5,6-tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5S)-N-(tert-Butoxycarbonyl)-3,4,5,6-tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one(220077-24-7)
• EPA Substance Registry System: (5S)-N-(tert-Butoxycarbonyl)-3,4,5,6-tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one(220077-24-7)

Safety Data

• Hazardous Substances Data: 220077-24-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(5S)-N-(tert-Butoxycarbonyl)-3,4,5,6-tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one is used as an intermediate in organic synthesis for the preparation of various pharmaceuticals and organic compounds. Its unique structure and Boc protecting group facilitate selective reactions and modifications, making it a valuable building block in the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (5S)-N-(tert-Butoxycarbonyl)-3,4,5,6-tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one is used as a research compound for exploring its potential biological activities and therapeutic applications. Its presence in natural products and pharmaceuticals suggests that it may possess beneficial properties that can be harnessed for the development of new drugs and treatments.
Used in Drug Development:
(5S)-N-(tert-Butoxycarbonyl)-3,4,5,6-tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one is also utilized in drug development as a candidate molecule for the discovery of novel therapeutic agents. Its potential biological activities and unique structural features make it an attractive target for further research and optimization to develop new drugs with improved efficacy and safety profiles.

InChI:InChI=1/C15H19NO4/c1-15(2,3)20-14(18)16-9-13(17)19-10-12(16)11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3/t12-/m1/s1

Upstream product

• 20989-17-7 (2S)-2-phenylglycinol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 144896-92-4 (5S)-5-phenylmorpholin-2-one 
• 56613-80-0 D-2-phenylglycinol 
• 121269-45-2 (R)-5-phenyl-3,4,5,6-tetrahydro-2H-1,4-oxazin-2-one 

Downstream Products

• 881099-31-6 (3S,5S)-3-(2-methylallyl)-5-phenyl-3,4,5,6-tetrahydro-1,4-oxazin-2-one 
• 1214274-52-8 (3S,5S)-3-allyl-5-phenylmorpholin-2-one 
• 122689-83-2 (3R,5R)-3-Benzyloxycarbonylmethyl-2-oxo-5-phenyl-morpholine-4-carboxylic acid tert-butyl ester 
• 122743-45-7 (3S,5R)-3-Benzyloxycarbonylmethyl-2-oxo-5-phenyl-morpholine-4-carboxylic acid tert-butyl ester 
• 119878-91-0 (E)-3-(3-(diethylphosphono)prop-2-en-1-yl)-4-(tert-butoxycarbonyl)-5-phenyl-2H-1,4-oxazin-2-one 

Relevant articles and documents

A mild approach to synthesise enantiopure glycine-derived 5-phenylthiomorpholinone

A seven-step synthetic route has been developed to access the labile C-3 unsubstituted 5-phenylthiomorpholinone system for the first time. The key step involved the nucleophilic ring opening of Boc-phenylmorpholinone to give the corresponding methyl ester. The sulfur introduction was accomplished through a Mitsunobu reaction to yield a thioacetate, which was then hydrolysed to provide the thiol acid. Cyclization of the thiol acid was achieved using DCC in the presence of DMAP, to give Boc-phenylthiomorpholinone and subsequent deprotection afforded the elusive C-3 unsubstituted 5-phenylthiomorpholinone.

Enantioselective Synthesis of α-Amino Acid Derivatives via the Stereoselective Alkylation of a Homochiral Glycine Enolate Synthon

A new synthetic method for the enantioselective preparation of α-amino acid derivatives is presented.The key step involves the diastereoselective alkylation of the new chiral glycine enolate synthons 7 and 8 providing alkylation adducts with de of > 97.6percent in good yields (73-90percent).The reactivities of the enolates of 7 and 8 were extraordinarily sensitive to the metal counterion and solvent.Experimental conditions are described to maintain high diastereoselectivities in the alkylation step for electrophiles varying from highly reactive (α-haloacetate esters) to less reactive (n-butyl iodide).The alkylation diastereoselectivities were established to be under kinetic control by equilibration experiments on selected alkylation products.A model is presented which hinges on an A(1,3) interaction between the termini of the N4-acyl protecting group and the C5-phenyl group of 7 and 8 which in turn dictates the ?-facial selectivity of the enolate.The model successfully accounts for the observed results and is corroborated by the conformation of an alkylation adduct as revealed by a single-crystal X-ray determination.A simple one-pot, three-step deprotection procedure provides the desired α-amino acid as the ethyl ester hydrochloride salts (60-80percent overall yield) with no attending racemization as determined by conversion of the amino acid esters to the corresponding (+)- or (-)-Mosher amides.

STEREOSELECTIVE ALKYLATION OF CHIRAL GLYCINE ENOLATE SYNTHONS. THE ENANTIOSELECTIVE SYNTHESIS O α-AMINO ACID DERIVATES

The highly stereoselective alkylation (percentde=99.6 to 97.6) o a new chiral glycine enolate synthon derived from D-2-phenylglycinol is described.Deprotection of the alkylation adducts in a one-pot, three-step procedure provides the ethyl ester hydrochloride salts of the corresponding α-amino acids with no attending racemization.