Provided are a method for producing a peptide compound including a step of using a condensed polycyclic aromatic hydrocarbon compound represented by Formula (1); a protective group-forming reagent including the compound; and the compound. In Formula (1), a ring A represents a condensed polycyclic aromatic hydrocarbon ring, Y.sup.A's each independently represent —CH.sub.2OH, —CH.sub.2NHR, —CH.sub.2SH, or —CH.sub.2X.sup.0, where R represents a hydrogen atom, an alkyl group, or an aralkyl group, and X.sup.0 represents Cl, Br, or I, k represents an integer of 1 to 5, n represents 1 or 2, and R.sup.A's each independently represent an aliphatic hydrocarbon group or an organic group having an aliphatic hydrocarbon group.

##STR00001##

Provided are a method for producing a peptide compound including a step of using a hydrazine derivative represented by Formula (1); a reagent for forming a protective group including the compound; and a hydrazine derivative. In Formula (1), a ring A represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, R represents a hydrogen atom, an amino protective group, an amino acid residue, or a peptide residue, k represents an integer of 1 to 5, n represents 1 or 2, and R.sup.A's each independently represent an aliphatic hydrocarbon group or an organic group having an aliphatic hydrocarbon group.

##STR00001##

The disclosure provides a method for preparing drug-linker MC-MMAF for antibody drug conjugates and intermediates therein. The preparation method of the present disclosure improves the reactivity of the N-terminal, thereby effectively controlling the occurrence of racemization; does not directly use the toxin MMAF, but uses fragmented peptides with lower toxicity, which minimizes the operational difficulty in scale-up production; no reverse phase is required and it is easy to prepare and operate.

A structure of the compound containing a diphenylmethane structure of the present invention is represented by General Formula (1). The compound containing a diphenylmethane structure of the present invention contains a hydroxyl group, an amino group, a substituted amino group, and an active group, and can be used as an amino acid or peptide C-terminal protection reagent. A peptide synthesis reaction using this protection carrier has a fast reaction speed and a high reagent utilization rate in a suitable solvent system; post-treatment is carried out by means of simple liquid-liquid extraction separation, i.e. effective purification can be carried out, and finally, a product with a high purity can be obtained; and during a synthesis process, the change in solubility is small and an operation process has a strong universality, and therefore, the present method can be developed into a universal production method.

An object of the present invention is to provide a method for producing a peptide with high purity and high efficiency, a protective group-forming reagent having excellent deprotective properties, and a novel condensed polycyclic compound. According to the present invention, there are provided a method for producing a peptide including a step of using a polycyclic compound represented by Formula (1), a protective group-forming reagent containing the polycyclic compound, and the polycyclic compound. At least one of R.sup.1 to R.sup.8 and R.sup.110 has R.sup.A, R.sup.A represents an aliphatic hydrocarbon group or an organic group having an aliphatic hydrocarbon group, and at least one aliphatic hydrocarbon group has 3 or more carbon atoms.

##STR00001##

The present invention relates to a novel synthesis method to form particular molecules. These molecules have multiple uses, most notably in the field of protecting groups used throughout organic and synthetic chemistry. The disclosed method is safer, more cost- and time-effective, and more amenable to large scale production than those currently known in the art. The protecting groups synthesized are useful in GAP peptide synthesis.

Provided are a method for producing a peptide compound including a step of using a condensed polycyclic aromatic hydrocarbon compound represented by Formula (1); a protective group-forming reagent including the compound; and the compound. In Formula (1), a ring A represents a condensed polycyclic aromatic hydrocarbon ring, Y.sup.A's each independently represent —OH, —NHR, —SH, or —X.sup.0, where X.sup.0 represents Cl, Br, or I, R.sup.A and R.sup.C each independently represent an aliphatic hydrocarbon group or an organic group having an aliphatic hydrocarbon group, R.sup.Bs' each independently represent a monovalent aliphatic hydrocarbon group, a (1+c)-valent aromatic group, or a (1+c)-valent heteroaromatic group, where, in a case where both a and c is 0, R.sup.B is a monovalent aliphatic hydrocarbon group, and the number of carbon atoms in at least one aliphatic hydrocarbon group is 12 or more.

##STR00001##

The present invention relates to a novel synthesis method to form particular molecules. These molecules have multiple uses, most notably in the field of protecting groups used throughout organic and synthetic chemistry. The disclosed method is safer, more cost- and time-effective, and more amenable to large scale production than those currently known in the art. The protecting groups synthesized are useful in GAP peptide synthesis.

Provided are a method for producing a peptide compound including a step of using a compound represented by Formula (1); a protective group-forming reagent including the compound; and the compound. At least one of R.sup.1 to R.sup.8 or Y.sup.2 has R.sup.A, R.sup.A represents an aliphatic hydrocarbon group or an organic group having an aliphatic hydrocarbon group, and the number of carbon atoms in at least one aliphatic hydrocarbon group is 12 or more. However, R.sup.A does not have a silyl group and a hydrocarbon group having a silyloxy structure.

##STR00001##

Peptides may be continuously produced by a method including the following steps (1), (A), (2), and (B): (1) performing a condensation reaction in a flow reactor to obtain an N-protected C-protected peptide in which an N-terminal amino group and C-terminal are protected by protecting groups, a side chain functional group is optionally further protected by a protecting group, and at least one of the C-terminal or the side chain functional group is protected by a pseudo-solid-phase protecting group (N-protected C-protected peptide), (A) washing a reaction mixture containing an N-protected C-protected peptide in a flow reactor and separating oil and water to separate an organic layer containing the N-protected C-protected peptide, (2) subjecting an organic layer containing an N-protected C-protected peptide to a reaction to remove a protecting group of an N-terminal amino group in a flow reactor to obtain a C-protected peptide in which an N-terminal amino group is not protected, C-terminal is protected by a protecting group, a side chain functional group is optionally further protected by a protecting group, and at least one of the C-terminal or the side chain functional group is protected by a pseudo-solid-phase protecting group (N-unprotected C-protected peptide), (B) subjecting a reaction mixture containing an N-unprotected C-protected peptide to washing and oil-water separation in a flow reactor to separate an organic layer containing the N-unprotected C-protected peptide.