L'invention concerne un procédé de préparation des produits (I) :

R étant hydrogène, alkyle, alcényle, cyano, formyle, carboxy, alcoxy carbonyle, [(arylalkyl) oxy] carbonyle ou halogène et R′ un groupe protecteur, caractérisé en ce que l'on traite un produit (II) :

par une base, puis par un borate d'alkyle, pour obtenir le produit (III) :

dont on protège l'hydroxy libre, puis que l'on hydrolyse.

Les produits (I) sont des intermédiaires utiles en synthèse organique.

An object of the present invention is to provide a novel tetrahydroazepine compound and a process for producing the same.

The present invention relates to a tetrahydroazepine compound represented by the formula (10) or a salt thereof, and a process for producing the said compound or a salt thereof. (In the formula,

R¹ is an optionally substituted alkyl group,

R² is an optionally substituted alkyl group and

one of the X-Y bond and the Y-Z bond is a carbon-carbon double bond and the other is a carbon-carbon single bond.)

A method for producing an alkylamine derivative having a urea bond represented by formula (I), or a salt thereof, comprises the following steps (a) and (b),

step (a): and

step (b): deprotecting as necessary the reaction product obtained in step (a). The production method suitable for industriallization of the alkylamine derivative having a urea bond represented by formula (I), which is a compound highly useful as an agent having CaSR agonist effects is provided.

An objective of the present invention is to provide novel cyclic depsipeptide derivatives and harmful organism control agents including the same as each other. Specifically, the present invention provides compounds represented by formula (1) or stereoisomers thereof, harmful organism control agents containing them, and a process for producing them.

Disclosed is a method for producing a compound having an amino group and/or a hydroxyl group from a substrate compound having an atomic group containing CO or CS by eliminating said atomic group. The substrate compound having an atomic group containing CO or CS (for example, an amide, a carbamate, or the like) is allowed to react with a compound expressed by formula (I) below, at a temperature of 120°C or lower, preferably in the presence of an ammonium salt, to eliminate said atomic group containing CO or CS. In formula (I) A may not be present, and in a case where A is present, A represents an alkyl group having 1 to 6 carbon atoms.



        H₂N-A-NH₂     (I)

To provide: a hydroxy group protecting agent which is stable and easy to use, does not have carcinogenicity, a tearing property or the like, and is inexpensive; and a hydroxy group protection method which enables the protection of a hydroxy group under acidic conditions. [Solution] A hydroxy group protecting agent in which at least one protecting group is bound to a nitrogen-containing electron-withdrawing heterocyclic ring through any one of an oxygen atom, a sulfur atom and a nitrogen atom. The heterocyclic ring is a triazine ring or the like, and the protecting group is a benzyl group or the like. Specifically, the hydroxy group protecting agent is 2,4,6-tribenzyloxy-1,3,5-triazine, 2,4,6-tris(4-methoxybenzyloxy)-1,3,5-triazine or the like. In addition, 2,4,6-tris(t-butoxy)-1,3,5-triazine or the like can also be used. For protecting a hydroxy group, a compound of interest which has a hydroxy group is reacted with the hydroxy group protecting agent under acidic conditions.

To deprotect an alcoholic hydroxyl group protected by a t-butyldimethylsilyl group without influencing a functional group unstable to an acid. In the presence of a solvent, an alcohol having a hydroxyl group protected by a t-butyldimethylsilyl group is deprotected in the presence of an acid or an acid salt having a pKa of from 1.0 to 3.0 in water.

An object of the present invention is to provide a novel method for producing a peptide utilizing a ligation reaction in which ligation efficiency is excellent and side reactions to other functional groups in the peptide are hard to occur, in comparison with the conventional native chemical ligation methods utilizing the thiol auxiliary group. The present invention provides a method for producing a peptide which comprises a step of causing a first peptide and a second peptide to react in the presence of a reducing agent to obtain a a ligated product of the first peptide and the second peptide, wherein the first peptide contains, at the C-terminal end, an amino acid derivative having a thioester group, and the second peptide contains, at the N-terminal end, a serine or threonine derivative having a thiol auxiliary group.

A dibenzofulvene amine adduct is removed by contacting a reaction mixture containing the dibenzofulvene amine adduct, which is obtained by reacting, for deprotection, an amino acid compound protected with an Fmoc group with an amine compound wherein a nitrogen atom has at least one hydrogen atom, with carbon dioxide, and removing the carbonate of the dibenzofulvene amine adduct. Alternatively, a dibenzofulvene amine adduct is removed by mixing a reaction mixture during a deprotection reaction of the amino acid compound protected with an Fmoc group, or after the reaction with an amine compound wherein a nitrogen atom has at least one hydrogen atom to give a mixture containing the dibenzofulvene amine adduct, contacting the mixture with carbon dioxide, and removing the carbonate of the dibenzofulvene amine adduct.