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Title: 4-cyano-3-hydroxybutanoyl hydrazines, derivatives and process for the preparation thereof

Patent ·
OSTI ID:873220
 [1];  [2]
  1. Haslett, MI
  2. East Lansing, MI
+ Show Author Affiliations

Novel 4-cyano-3-hydroxybutanoyl hydrazides (10), particularly R-chiral intermediates are described. The intermediates are useful in preparing (R)-3-hydroxy-4-trimethylaminobutyric acid (L-carnitine) and R-4-amino-3-hydroxybutyric acid (GABOB) and chiral chemical intermediates which are medically useful.

Research Organization:
Michigan State Univ., East Lansing, MI (United States)
DOE Contract Number:
FG02-89ER14029
Assignee:
Board of Trustees Operating Michigan State University (East Lansing, MI)
Patent Number(s):
US 6114566
OSTI ID:
873220
Country of Publication:
United States
Language:
English

References (36)

Simple Three-Step Synthesis of ( R )- and ( S )-4-Amino-3-hydroxybutanoic Acid (GABOB) by Stereoselective Aldol Addition journal January 1989
A mild hydration of nitriles into amides journal February 1994
Baker's Yeast Reduction of N -Protected Methyl 4-Amino-3-oxobutanoates and 3-oxopentanoates journal January 1992
Theβ-Lactone Route to a Totally Stereoselective Synthesis of Carnitine Derivatives journal July 1996
(-)-β-Pinene as chiral promoter. Stereospecific access to (-)-γ-amino-β()-hydroxybutyric acid (gabob) and ()-carnitine.2 journal January 1985
A convenient preparation of optically pure 3-hydroxyglutaric acid derivatives journal March 1994
A simple total synthesis of both enantiomers of γ-amino-β-hydroxybutanoic acid (GABOB) by enzymatic kinetic resolution of cyanohydrin acetates journal January 1990
An efficient synthesis of (r)-carnitine journal February 1992
Synthesis of a chiral phospholipase-C and D insensitive membrane probe with excimer emission properties journal February 1998
Immobilized benzylpenicillin acylase: Application to the synthesis of optically active forms of carnitin and propranalol journal January 1986
Bifunctional chiral synthons via biochemical methods. 5. Preparation of (S)-ethyl hydrogen-3-hydroxyglutarate, key intermediate to (R)-4-amino-3-hydroxybutyric acid and L-carnitine. journal January 1984
Practical synthesis of (R)-γ-amino-β-hydroxybutanoic acid (GABOB) from (R)-epichlorohydrin journal January 1987
Efficient Asymmetric Hydrogenation of .ALPHA.-Amino Ketone Derivatives. A Highly Enantioselective Synthesis of Phenylephrine, Levamisole, Carnitine and Propranolol. journal January 1995
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Synthesis of (R)-(-)-γ-amino β-hydroxy Butyric Acid (GABOB) journal December 1989
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A convenient synthesis of R-(−)-carnitine from R-(−)-epichlorohydrin journal August 1997
Total synthesis of (R)-glycerol acetonide and the antiepileptic and hypotensive drug (-)-.gamma.-amino-.beta.-hydroxybutyric acid (GABOB): use of vitamin C as a chiral starting material journal September 1980
Intramolecular SN2 ring opening of a cyclic sulfate: synthesis of erythro-(−)-6-acetoxy-5-hexadecanolide—a major component of mosquito oviposition attractant pheromone journal February 1997
Syntheses of the enantiomers of carnitine and 4-methylcarnitine via the chromatographic resolution of .gamma.-(dimethylamino)-.beta.-hydroxy ester precursors journal May 1987
Short and practical syntheses of(R)-(−)-carnitine and (R)-(−)-γ-amino-β-hydroxybutyric acid (GABOB) journal January 1993
The synthesis of (4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate, a key intermediate for the preparation of CI-981, a highly potent, tissue selective inhibitor of HMG-CoA reductase journal April 1992
Simple synthesis of (R)-Carnitine from d-Galactono-1,4-lactone journal January 1992
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Organic Syntheses Hofmann Rearrangement Under Mildly Acidic Conditions Using [I,I-Bis(Trifluoroacetoxy)]Iodobenzene: Cyclobutylamine Hydrochloride from Cyclobutanecarboxamide book April 2003
Systemic Carnitine Deficiency — A Treatable Inherited Lipid-Storage Disease Presenting as Reye's Syndrome journal December 1980
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Reviews journal January 1991
Synthesis of enantiomerically pure .gamma.-amino-.beta.-hydroxybutyric acid using malic acid as the chiral precursor journal December 1985
Direct Conversion of ( S )-3-Hydroxy-γ-butyrolactone to Chiral Three-Carbon Building Blocks journal February 1999
Lipid-lowering effect of carnitine in chronically uremic patients treated with maintenance hemodialysis journal July 1980
Enzymic hydrolysis of alkyl 3,4-epoxybutyrates. A new route to (R)-(-)-carnitine chloride journal January 1988

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Related Subjects

4-cyano-3-hydroxybutanoyl
hydrazines
derivatives
process
preparation
novel
hydrazides
10
particularly
r-chiral
intermediates
described
useful
preparing
-3-hydroxy-4-trimethylaminobutyric
acid
l-carnitine
r-4-amino-3-hydroxybutyric
gabob
chiral
chemical
medically
chemical intermediate
medically useful
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