GB989537A - Resolution of n-acyl-dl-tryptophans - Google Patents

Resolution of n-acyl-dl-tryptophans

Info

Publication number
GB989537A
GB989537A GB3536761A GB3536761A GB989537A GB 989537 A GB989537 A GB 989537A GB 3536761 A GB3536761 A GB 3536761A GB 3536761 A GB3536761 A GB 3536761A GB 989537 A GB989537 A GB 989537A
Authority
GB
United Kingdom
Prior art keywords
enantiomer
acyl
enantiomers
ammonium
resolving
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
GB3536761A
Inventor
Ichiro Sasaji
Ko Ohno
Jiro Kato
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.)
Ajinomoto Co Inc
Original Assignee
Ajinomoto Co Inc
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 Ajinomoto Co Inc filed Critical Ajinomoto Co Inc
Priority to GB3536761A priority Critical patent/GB989537A/en
Publication of GB989537A publication Critical patent/GB989537A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane

Landscapes

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

Abstract

The invention comprises ammonium N-acyl-DL-tryptophanates, and the specific D- and L-enantiomers thereof described in the examples of the Specification; and a process for resolving a racemic ammonium N-acyl-tryptophanate by contacting a supersaturated solution thereof with one enantiomer to cause crystallization of said enantiomer, and thereafter separating said crystals from the mother liquor. The process may be effected by adding a crystal or a solution of the one enantiomer to a cooled or subsequently cooled solution of the racemate, whereby the enantiometer crystallizes. The mother liquor may then be contacted with the racemate before or after warming, and the resulting solution cooled to cause crystallization of the other enantiomer, which crystallization may be assisted by seeding with crystals of said enantiomer. Repetition of these processes gives continued production of the two enantiomers. Preferred solvents for use in the process are water, aqueous methanol and aqueous ethanol. The invention also comprises a process for resolving an N-acyl-tryptophan, by treating it with ammonia to give the ammonium salt, resolving this by the above-described process, and decomposing the D- and L-ammonium salts with dilute acid to produce the D- and L-N-acyltryptophans. Ammonium salts of the enantiomers may also be prepared from the enantiomers and ammonia. N-acyl-tryptophanates used are the formyl, acetyl and propionyl compounds. Specification 745,097 is referred to.
GB3536761A 1961-09-29 1961-09-29 Resolution of n-acyl-dl-tryptophans Expired GB989537A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3536761A GB989537A (en) 1961-09-29 1961-09-29 Resolution of n-acyl-dl-tryptophans

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3536761A GB989537A (en) 1961-09-29 1961-09-29 Resolution of n-acyl-dl-tryptophans

Publications (1)

Publication Number Publication Date
GB989537A true GB989537A (en) 1965-04-22

Family

ID=10376945

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3536761A Expired GB989537A (en) 1961-09-29 1961-09-29 Resolution of n-acyl-dl-tryptophans

Country Status (1)

Country Link
GB (1) GB989537A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3039785A1 (en) * 1980-10-22 1982-05-27 Willi 2000 Hamburg Ellenberger L-Tryptophan prodn. from indole - via di:ethylamino:methyl-indole and DL-acetyl-tryptophan
EP2334620B1 (en) * 2008-09-05 2018-09-05 Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. Process for enantioseparation of chiral systems with compound formation using two subsequent crystallization steps

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3039785A1 (en) * 1980-10-22 1982-05-27 Willi 2000 Hamburg Ellenberger L-Tryptophan prodn. from indole - via di:ethylamino:methyl-indole and DL-acetyl-tryptophan
EP2334620B1 (en) * 2008-09-05 2018-09-05 Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. Process for enantioseparation of chiral systems with compound formation using two subsequent crystallization steps

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