500720-15-0

Basic information

• Product Name: Carbamic acid, (tetrahydro-3-oxo-2H-1,2-oxazin-4-yl)-, 1,1-dimethylethyl ester
• Synonyms: Carbamic acid, (tetrahydro-3-oxo-2H-1,2-oxazin-4-yl)-, 1,1-dimethylethyl ester;tert-butylN-(3-oxo-1,2-oxazinan-4-yl)carbaMate;tert-Butyl (3-oxo-1,2-oxazinan-4-yl)carbamate;tert-butyl N-(3-oxooxazinan-4-yl)carbamate
• CAS NO: 500720-15-0
• Molecular Formula: C9H16N2O4
• Molecular Weight: 216.23434
• Product Categories: N-BOC
• Mol File: 500720-15-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Carbamic acid, (tetrahydro-3-oxo-2H-1,2-oxazin-4-yl)-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (tetrahydro-3-oxo-2H-1,2-oxazin-4-yl)-, 1,1-dimethylethyl ester(500720-15-0)
• EPA Substance Registry System: Carbamic acid, (tetrahydro-3-oxo-2H-1,2-oxazin-4-yl)-, 1,1-dimethylethyl ester(500720-15-0)

Safety Data

• Hazardous Substances Data: 500720-15-0(Hazardous Substances Data)

Upstream product

• 500720-14-9 methyl N-BOC-α-amino-γ-aminooxybutyrate 
• 500720-13-8 methyl N-BOC-α-amino-γ-phthalimidooxybutyrate 
• 500720-12-7 methyl 2-tert-butoxycarbonylamino-4-methanesulfonylooxybutyrate 
• 120042-12-8 methyl 2-(tert-butoxycarbonylamino)-4-hydroxy-butanoate 
• 24424-99-5 di-tert-butyl dicarbonate 

Relevant articles and documents

Cyclic hydroxamates, especially multiply substituted [1,2]oxazinan-3-ones

Routes to putative N-acyl-D-ala-D-ala surrogates, beginning with the conversion of 4-, 5-, and 6-membered lactones into 5-, 6-, and 7-membered cyclic hydroxamates, are reported. The key step of the synthesis is trimethylaluminium-promoted cyclization of an ω-aminooxyester. The 7-membered cyclic hydroxamate crystallizes in a chair conformation. Extension of the reaction sequence to homoserine or homoserine lactone leads to cyclocanaline and N-acylated cyclocanalines. The 4-phenylacetamido derivative of cyclocanaline crystallizes in a boat conformation. The attachment of a 2-carboxypropyl substituent to the ring nitrogen of a 4-acylaminocyclocanaline has been effected, prior to cyclization, by coupling of the acyclic aminooxyester precursor to the triflate of benzyl lactate or, after cyclization, by coupling to tert-butyl α-bromopropionate in the presence of potassium fluoride - alumina, followed by removal of the protecting group in each case. A six-membered homolog of the antibiotic lactivicin has been synthesized by the reaction of 4-phenylacetamidocyclocanaline with benzyl 2-oxoglutarate in the presence of carbodiimide, followed by hydrogenolysis. Starting with methyl 2,4-dibromo-2,4-dideoxy-L-erythronate, which is available in two steps from L-ascorbic acid, these reaction sequences have been applied to the stereospecific synthesis of a D-alanine derivative whose nitrogen atom is enclosed within a 3,4-disubstituted [1,2]oxazinan-3-one.

Method for synthesizing oxazinones

New methods and intermediates are discussed for the stereospecific synthesis of oxazinone compounds.