119878-90-9

Basic information

• Product Name: (5R)-N-(TERT-BUTOXYCARBONYL)-3,4,5,6-TETRAHYDRO-5-PHENYL-4(H)-1,4-OXAZIN-2-ONE
• Synonyms: (5R)-2-Oxo-5-phenyl-4-morpholinecarboxylic acid tert-butyl ester;(R)-2-Oxo-5-phenyl-4-morpholinecarboxylic acid tert-butyl ester;(R)-TERT-BUTYL 2-OXO-5-PHENYLMORPHOLINE-4-CARBOXYLATE;(5R)-N-(TERT-BUTOXYCARBONYL)-3,4,5,6-TETRAHYDRO-5-PHENYL-4(H)-1,4-OXAZIN-2-ONE;(5R)-N-TERT BUTYLOXYCARBONYL -3,4,5,6-TETRAHYDRO-5-PHENYL-4(H)-1,4-OXAZIN-2-ONE
• CAS NO: 119878-90-9
• Molecular Formula: C₁₅H₁₉NO₄
• Molecular Weight: 277.32
• Mol File: 119878-90-9.mol

Chemical Properties

• Melting Point: 87-89℃
• Boiling Point: 382.7 °C at 760 mmHg
• Flash Point: 185.2 °C
• Appearance: /
• Density: 1.172
• CAS DataBase Reference: (5R)-N-(TERT-BUTOXYCARBONYL)-3,4,5,6-TETRAHYDRO-5-PHENYL-4(H)-1,4-OXAZIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (5R)-N-(TERT-BUTOXYCARBONYL)-3,4,5,6-TETRAHYDRO-5-PHENYL-4(H)-1,4-OXAZIN-2-ONE(119878-90-9)
• EPA Substance Registry System: (5R)-N-(TERT-BUTOXYCARBONYL)-3,4,5,6-TETRAHYDRO-5-PHENYL-4(H)-1,4-OXAZIN-2-ONE(119878-90-9)

Safety Data

• Hazardous Substances Data: 119878-90-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(5R)-N-(TERT-BUTOXYCARBONYL)-3,4,5,6-TETRAHYDRO-5-PHENYL-4(H)-1,4-OXAZIN-2-ONE is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure and reactivity make it a valuable component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, (5R)-N-(TERT-BUTOXYCARBONYL)-3,4,5,6-TETRAHYDRO-5-PHENYL-4(H)-1,4-OXAZIN-2-ONE serves as a crucial building block for the creation of agrochemicals. Its application aids in the development of pesticides, herbicides, and other crop protection agents, enhancing agricultural productivity and crop protection strategies.
Used as a Reagent in Organic Synthesis:
(5R)-N-(TERT-BUTOXYCARBONYL)-3,4,5,6-TETRAHYDRO-5-PHENYL-4(H)-1,4-OXAZIN-2-ONE is utilized as a reagent in organic synthesis for its ability to participate in a variety of chemical reactions. Its use facilitates the construction of complex molecular frameworks and the synthesis of target organic compounds in research and industrial applications.

Upstream product

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

Downstream Products

• 121269-48-5 (3R,5R)-2,3,5,6-tetrahydro-3-methyl-5-phenyl-N-(tert-butyloxycarbonyl)-4H-1,4-oxazin-2-one 
• 121348-76-3 (3S,5R)-2,3,5,6-tetrahydro-3-methyl-5-phenyl-N-(tert-butyloxycarbonyl)-4H-1,4-oxazin-2-one 
• 121269-58-7 (R)-2-((R)-2-Hydroxy-1-phenyl-ethylamino)-4-methyl-pent-4-enoic acid ethyl ester; hydrochloride 
• 121348-81-0 (3S,5R)-2,3,5,6-tetrahydro-3-(n-butyl)-5-phenyl-N-(tert-butyloxycarbonyl)-4H-1,4-oxazin-2-one 
• 121348-79-6 (3S,5R)-2,3,5,6-tetrahydro-3-(2-methylprop-1-en-3-yl)-5-phenyl-N-(tert-butyloxycarbonyl)-4H-1,4-oxazin-2-one 
• 121348-80-9 (3S,5R)-2,3,5,6-tetrahydro-5-phenyl-3-prop-1-en-3-yl-N-(tert-butyloxycarbonyl)-4H-1,4-oxazin-2-one 
• 158221-60-4 (4R,9aR)-9a-Benzyl-4-phenylhexahydropyrido<2,1-c><1,4>oxazin-1-one 
• 158221-59-1 (4R,9aS)-9a-Ethyl-4-phenylhexahydropyrido<2,1-c><1,4>oxazin-1-one 
• 874368-21-5 (4R,9aR)-9a-Ethyl-4-phenylhexahydropyrido<2,1-c><1,4>oxazin-1-one 
• 158221-57-9 (4R,9aS)-4-Phenylhexahydropyrido<2,1-c><1,4>oxazin-1-one 
• 158341-07-2 (4R,9aR)-4-Phenylhexahydropyrido<2,1-c><1,4>oxazin-1-one 
• 158221-58-0 (4R,9aS)-9a-Methyl-4-phenylhexahydropyrido<2,1-c><1,4>oxazin-1-one 
• 874368-20-4 (4R,9aR)-9a-Methyl-4-phenylhexahydropyrido<2,1-c><1,4>oxazin-1-one 
• 874368-18-0 (4R,9aS)-9a-propyl-4-phenylhexahydropyrido[2,1-c][1,4]oxazin-1-one 

Relevant articles and documents

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.