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Title: Method for conversion of .beta.-hydroxy carbonyl compounds

Abstract

A process is disclosed for conversion of salts of .beta.-hydroxy carbonyl compounds forming useful conversion products including, e.g., .alpha.,.beta.-unsaturated carbonyl compounds and/or salts of .alpha.,.beta.-unsaturated carbonyl compounds. Conversion products find use, e.g., as feedstock and/or end-use chemicals.

Inventors:
 [1];  [1];  [2];  [2];  [2];  [2]
  1. Richland, WA
  2. Kennewick, WA
Publication Date:
Research Org.:
Method for conversion of .beta.-hydroxy carbonyl compounds
Sponsoring Org.:
USDOE
OSTI Identifier:
1014395
Patent Number(s):
7,687,661
Application Number:
US Patent Application 11/377,096
Assignee:
Battelle Memorial Institute (Richland, WA)
DOE Contract Number:  
AC06-76RL01830
Resource Type:
Patent
Country of Publication:
United States
Language:
English

Citation Formats

Lilga, Michael A, White, James F, Holladay, Johnathan E, Zacher, Alan H, Muzatko, Danielle S, and Orth, Rick J. Method for conversion of .beta.-hydroxy carbonyl compounds. United States: N. p., 2010. Web.
Lilga, Michael A, White, James F, Holladay, Johnathan E, Zacher, Alan H, Muzatko, Danielle S, & Orth, Rick J. Method for conversion of .beta.-hydroxy carbonyl compounds. United States.
Lilga, Michael A, White, James F, Holladay, Johnathan E, Zacher, Alan H, Muzatko, Danielle S, and Orth, Rick J. Tue . "Method for conversion of .beta.-hydroxy carbonyl compounds". United States. https://www.osti.gov/servlets/purl/1014395.
@article{osti_1014395,
title = {Method for conversion of .beta.-hydroxy carbonyl compounds},
author = {Lilga, Michael A and White, James F and Holladay, Johnathan E and Zacher, Alan H and Muzatko, Danielle S and Orth, Rick J},
abstractNote = {A process is disclosed for conversion of salts of .beta.-hydroxy carbonyl compounds forming useful conversion products including, e.g., .alpha.,.beta.-unsaturated carbonyl compounds and/or salts of .alpha.,.beta.-unsaturated carbonyl compounds. Conversion products find use, e.g., as feedstock and/or end-use chemicals.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2010},
month = {3}
}

Patent:

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Works referenced in this record:

A Study of some rare Earth Compounds.
journal, May 1917

  • Grant, A. J.; James, C.
  • Journal of the American Chemical Society, Vol. 39, Issue 5
  • DOI: 10.1021/ja02250a009

Preparation of acetamide by the action of ammonium hydroxide and ethyl acetate
journal, November 1907


Novel stereospecific dehydration of β-hydroxy-α-amino acids using Martin's sulfurane
journal, November 2002


Stereospecific introduction of double bounds via thermolysis of .beta.-lactones
journal, March 1972

  • Adam, Waldemar; Baeza, Jaime; Liu, Ju-Chao
  • Journal of the American Chemical Society, Vol. 94, Issue 6
  • DOI: 10.1021/ja00761a036

Polymer-supported alkyl azodicarboxylates for Mitsunobu reactions
journal, May 1989

  • Arnold, Lee D.; Assil, Hanaa I.; Vederas, John C.
  • Journal of the American Chemical Society, Vol. 111, Issue 11
  • DOI: 10.1021/ja00193a032

362. The dehydration of β-hydroxy-esters
journal, January 1932


Synthesis of the stereoisomers of a novel antibacterial agent and interpretation of their relative activities in terms of a theoretical model of the penicillin receptor
journal, April 1994

  • Wolfe, Saul; Zhang, Caijun; Johnston, Blair D.
  • Canadian Journal of Chemistry, Vol. 72, Issue 4
  • DOI: 10.1139/v94-134

Studies on the Stability of Amides. IV. Intramolecular Hydroxyl Group Participation in the Acidic Hydrolysis of Aliphatic Amides
journal, January 1972

  • Yamana, Tsukinaka; Tsuji, Akira; Mizukami, Yuzo
  • CHEMICAL & PHARMACEUTICAL BULLETIN, Vol. 20, Issue 6
  • DOI: 10.1248/cpb.20.1217

Conversion of serine .beta.-lactones to chiral .alpha.-amino acids by copper-containing organolithium and organomagnesium reagents
journal, July 1987

  • Arnold, Lee D.; Drover, John C. G.; Vederas, John C.
  • Journal of the American Chemical Society, Vol. 109, Issue 15
  • DOI: 10.1021/ja00249a031

Mechanism of formation of serine β-lactones by Mitsunobu cyclization: synthesis and use of L -serine stereospecifically labelled with deuterium at C-3
journal, April 1986

  • Ramer, Shawn E.; Moore, Richard N.; Vederas, John C.
  • Canadian Journal of Chemistry, Vol. 64, Issue 4
  • DOI: 10.1139/v86-113

Ueber die Darstellung der Amide einbasischer Säuren der aliphatischen Reihe
journal, January 1882


Ueber einige Derivate des Kyanmethins
journal, January 1885


CATALYSIS OF THE FORMATION AND HYDROLYSIS OF ACETAMIDE BY ACETIC ACID 1
journal, October 1922

  • Noyes, William A.; Goebel, Walter F.
  • Journal of the American Chemical Society, Vol. 44, Issue 10
  • DOI: 10.1021/ja01431a027

Conversion of serine to stereochemically pure .beta.-substituted .alpha.-amino acids via .beta.-lactones
journal, November 1985

  • Arnold, Lee D.; Kalantar, Thomas H.; Vederas, John C.
  • Journal of the American Chemical Society, Vol. 107, Issue 24
  • DOI: 10.1021/ja00310a058

A New Synthetic Route to β-Unsubstituted β-Lactones by Intramolecular Cyclization
journal, June 2000


Carbonyl Reactions. VI. Evidence for Alternate Mechanisms for the Dehydration of β-Hydroxy Ketones 1
journal, October 1958

  • Noyce, Donald S.; Reed, Wilmer L.
  • Journal of the American Chemical Society, Vol. 80, Issue 20
  • DOI: 10.1021/ja01553a056

Synthesis, conformational analysis and biological activities of lanthionine analogs of a cell adhesion modulator
journal, January 2001

  • Li, Haitao; Jiang, Xiaohui; Goodman, Murray
  • Journal of Peptide Science, Vol. 7, Issue 2
  • DOI: 10.1002/psc.296

The Production of Acylamines by the Interaction of Sodium Salts of Monobasic Acids and Amine Hydrochlorides.
journal, August 1902

  • Dunlap, Frederick L.
  • Journal of the American Chemical Society, Vol. 24, Issue 8
  • DOI: 10.1021/ja02022a008

Solubilities of some Normal Aliphatic Amides, Anilides, and N,N-Diphenylamides
journal, September 1943

  • Ralston, A. W.; Hoerr, C. W.; Pool, W. O.
  • The Journal of Organic Chemistry, Vol. 08, Issue 5
  • DOI: 10.1021/jo01193a011

Facile Chemoselective Synthesis of Dehydroalanine-Containing Peptides
journal, November 2000

  • Okeley, Nicole M.; Zhu, Yantao; van der Donk, Wilfred A.
  • Organic Letters, Vol. 2, Issue 23
  • DOI: 10.1021/ol006485d

Synthesis and Structure of ( E )-3-Phenylmethylene-2-oxetanone: Comments on the Stability of Methylene β-Lactones
journal, January 1990

  • Campi, Eva M.; Dyall, Kenneth; Fallon, Gary
  • Synthesis, Vol. 1990, Issue 09
  • DOI: 10.1055/s-1990-27035

β-Propiolactone. I. Polymerization Reactions
journal, March 1948

  • Gresham, T. L.; Jansen, J. E.; Shaver, F. W.
  • Journal of the American Chemical Society, Vol. 70, Issue 3
  • DOI: 10.1021/ja01183a030

The α,β,γ-Triphenylbutyric Acids and Related Compounds 1
journal, December 1944

  • Crawford, H. Marjorie; Davidson, Jean Clarke; Plunkett, Mary Alys
  • Journal of the American Chemical Society, Vol. 66, Issue 12
  • DOI: 10.1021/ja01240a003

Synthesis and structural analysis of dehydrophenylalanine cyclophanes
journal, January 2002

  • Gibson (née Thomas), Susan E.; Jones, Jerome O.; Kalindjian, S. Barret
  • Chem. Commun., Issue 17
  • DOI: 10.1039/B205752M

Reaction of N-trityl amino acids with BOP: Efficient synthesis of t-butyl esters as well as N-trityl serine- and threonine-β-lactones
journal, June 1996


A new and efficient preparation of α,β-dehydroamino acids
journal, May 1995


The Preparation of Aliphatic Amides
journal, May 1931

  • Mitchell, James A.; Reid, E. Emmet.
  • Journal of the American Chemical Society, Vol. 53, Issue 5
  • DOI: 10.1021/ja01356a037

Total synthesis of somamide A, an Ahp (3-amino-6-hydroxy-2-piperidone)-containing cyclic depsipeptide
journal, November 2002