Production of mixed acid anhydride and amide compound

Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...

Reexamination Certificate

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Other Related Categories

C546S245000, C546S312000, C546S316000, C548S195000, C548S200000, C548S326500, C548S333500, C548S965000, C548S966000, C549S069000, C549S078000, C549S480000, C549S487000, C564S144000

Type

Reexamination Certificate

Status

active

Patent number

06927290

Description

ABSTRACT:
There is disclosed an advantageous mixed acid anhydride production method of formula (1):in-line-formulae description="In-line Formulae" end="lead"?R1C(O)OY(O)n(R2)p  (1)in-line-formulae description="In-line Formulae" end="tail"?wherein R1, R2and Y denote the same as defined below, n and p denote an integer of 1 or 2, which is characterized by adding a carboxylic acid of formula (2);in-line-formulae description="In-line Formulae" end="lead"?R1COOH  (2)in-line-formulae description="In-line Formulae" end="tail"?wherein R1denotes a hydrogen atom, an optionally substituted alkyl group or the like, an organic base to a solution of a carboxylic acid activating agent of formula (3);in-line-formulae description="In-line Formulae" end="lead"?(R2)pY(O)nX  (3)in-line-formulae description="In-line Formulae" end="tail"?wherein R2denotes an optionally substituted aliphatic hydrocarbyl group or the like, Y denotes a carbon atom, a phosphorus atom, or a sulfur atom, and X denotes a chlorine atom or the like.

REFERENCES:
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patent: 06-184054 (1994-07-01), None
patent: 10-175955 (1998-06-01), None
T. Applewhite et al., “Suppression of Racemization During Peptide Syntheses”,Tetrahedron Letters, No. 15, 1964, pp. 819-825.
G. Anderson et al., “A Reinvestigation of the Mixed Carbonic Anhydride Method of Peptide Synthesis”,Journal of the American Chemical Society, Sep. 13, 1967, pp. 5012-5017.
N. Albertson, “Synthesis of Peptides with Mixed Anhydrides”,Organic Reactions, vol. 12, 1962, pp. 157-355.
E.J. Bourne et al.,Journal of the American Chemical Society, 1954, pp. 2006-2012.
Urbanski et al.,Polish Journal of Chemistry, vol. 58, 1984, pp. 1227-1229.
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Webster's II New Riverside University Dictionary, p. 77 (definition of “add”) and p. 1160 (definition of “sum”). Houghton Mifflin Company, 1994.

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