GB865157A - Derivatives of dl-lysine - Google Patents

Derivatives of dl-lysine

Info

Publication number
GB865157A
GB865157A GB22205/57A GB2220557A GB865157A GB 865157 A GB865157 A GB 865157A GB 22205/57 A GB22205/57 A GB 22205/57A GB 2220557 A GB2220557 A GB 2220557A GB 865157 A GB865157 A GB 865157A
Authority
GB
United Kingdom
Prior art keywords
caproic acid
anion
amino
acid
betain
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB22205/57A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB865157A publication Critical patent/GB865157A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises processes for the production of (1) a -amino-e -trimethylamino caproic acid by reacting an excess of benzylamine at elevated temperature with an e -acylamino (or aroylamino)-a -bromo- (or chloro) caproic acid in solution to give e -acylamino-(or aroylamino)-a -dibenzyl-aminocaproic acid, hydrolysing this compound to give e -amino-a -dibenzylamino-caproic acid, methylating this last mentioned compound to give e -trimethylaminoa - dibenzylaminocaprioc acid which has one quaternary ammonium function and liberating the a -amino group of the last mentioned compound by hydrogenolisis, the resulting compound being recovered in the form of a betain or in association with an anion; (2) a -trimethylamino-e -amino-caproic acid by converting an a -bromo- (or chloro)-e -acylamino (or aroylamino)- caproic acid into a -amino-e -acylamino- (or aroylamino)-caproic acid by means of ammonia, methylating the a -amino group, removing the acyl or aroyl group by hydrolysis and recovering the resulting compound in the form of a betain or in association with an anion and (3) a ,e -bis-(trimethylamino) caproic acid by methylating the product of either of the two previous processes, the resulting compound being recovered in the form of a betain in association with an anion or in association with an anion for each of the quaternary ammonium functions. The sequence of steps together with other possible sequences is shown in the reaction scheme on next page: The invention includes also compounds of the formula V together with the corresponding quarternary salt and its dihydrochloride and diflavianate. VIII together with the corresponding quaternary salt and its dehydrochloride and diflavianate, X, where Y is an anion, particularly of hydrochloric or flavianic acid, together with the corresponding betain and IV together with the corresponding dihydrochloride, Examples describe the preparation of the following compounds in the following sequences: I to II to III to IV to V to X and I to VI to VII to VIII starting from a -bromo-E-benyozlamino-caproic acid and IX to X starting from DL-lysine. <FORM:0865157/IV (b)/1>
GB22205/57A 1956-07-17 1957-07-12 Derivatives of dl-lysine Expired GB865157A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR865157X 1956-07-17

Publications (1)

Publication Number Publication Date
GB865157A true GB865157A (en) 1961-04-12

Family

ID=9344208

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22205/57A Expired GB865157A (en) 1956-07-17 1957-07-12 Derivatives of dl-lysine

Country Status (1)

Country Link
GB (1) GB865157A (en)

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