Showing papers by "Kunisuke Izawa published in 1989"

Production of hydroxy-n-acyl-alpha-amino acid derivative

Abstract: PURPOSE: To readily and efficiently obtain a compound having many bioactivities and useful as synthetic intermediate of various bioactive substances by reacting 2-butene-1,4-diol with carbon monoxide and acid amide in the presence of cobalt catalyst. CONSTITUTION: 2-butene-1,4-diol is reacted with carbon monoxide and acid amide in the presence of cobalt catalyst in a solvent such as tetrahydrofuran at 50-200°C to obtain a compound expressed by formula I or formula II (R 1 is 1-20C alkyl, phenyl, substituted phenyl, naphthyl, substituted naphthyl or 1-20C alkenyl; n is integer; m is 1 or 2). 2-butene-1,4-diol and acid amide are used in a molar ratio of 1 :1, on the contrary, excess amount of carbon monoxide to 2-butene-1,4-diol and acid amide, and catalyst of 1/10-1 /10000 molar ratio to raw material, are respectively used. COPYRIGHT: (C)1991,JPO&Japio

Production of hydroxy-n-acyl-alpha-amino acid derivative, oligomer and lactone thereof

Abstract: PURPOSE: To readily and efficiently obtain a compound useful as a synthetic intermediate for various physiologically active substances from an inexpensive raw material by reacting a cyclic acetal or enol ether with carbon monoxide and an acid amide in the presence of a cobalt catalyst. CONSTITUTION: A cyclic acetal expressed by formula I (R 1 is H or 1-10C alkyl; n is 0 or 1) is reacted with carbon monoxide and an acid amide in the presence of a cobalt catalyst in a solvent, such as THF, at 50-200°C to provide the objective substance expressed by formula II or III (R 2 is H or protecting group; R 3 is 1-20C alkyl, substituted phenyl, substituted naphthyl or 1-20C alkenyl; m is an integer of ≥1; n is 0 or 1). The cyclic acetal and acid amide are used at 1:1 molar ratio and the catalyst is used at (1/10)-(1/10000) molar ratio based on the raw material. A cyclic enol ether expressed by formula IV (R 4 is H or carboxy) is used as a starting material to carry out reaction similar to that described above to afford a compound expressed by formula V or VI. COPYRIGHT: (C)1990,JPO&Japio

Novel amino acid derivative, its production and use thereof

Abstract: NEW MATERIAL:The amino acid derivative expressed by formula I (R is H or organic group eliminable under reducing or oxidizing condition; R is H or carboxyl-protecting group; R is H or OH-protecting group) wherein the steric configuration of 3-site is (S)-configuration. EXAMPLE:Methyl-(2S,3S)-3-acetoxypyroglutamate. USE:A drug. A synthetic intermediate for novel carbapenam or carbapenem of formula II (R =R ; R is ethyl, i-propyl, etc.) useful as various drugs such as beta-hydroxyglutamic acid acting to cerebral nerve and expected to be useful as a remedy for cerebronervous system or beta-lactam substance having excellent antibacterial activity. PREPARATION:A compound of formula I wherein the configuration of 2-site is (S) can be produced by producing a pyrrolidone derivative of formula II (R is H or CH3) having (S) configuration at 4-site from L-malic acid, cooling the derivative to -78 deg.C and reacting successively with O3 and diazomethane to effect oxidative cleavage reaction.