GB707903A - Improvements in or relating to the resolution of isomeric mixtures of 1-p-nitrophenyl-2-aminopropane-1,3-diol - Google Patents

Improvements in or relating to the resolution of isomeric mixtures of 1-p-nitrophenyl-2-aminopropane-1,3-diol

Info

Publication number
GB707903A
GB707903A GB11057/51A GB1105751A GB707903A GB 707903 A GB707903 A GB 707903A GB 11057/51 A GB11057/51 A GB 11057/51A GB 1105751 A GB1105751 A GB 1105751A GB 707903 A GB707903 A GB 707903A
Authority
GB
United Kingdom
Prior art keywords
isomers
diol
amino
aminopropane
nitrophenyl
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
GB11057/51A
Inventor
Bruce Norman Feitelson
Vladimir Petrow
Oliver Stephenson
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.)
BDH Chemicals Ltd
Original Assignee
BDH Chemicals Ltd
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 BDH Chemicals Ltd filed Critical BDH Chemicals Ltd
Priority to GB11057/51A priority Critical patent/GB707903A/en
Publication of GB707903A publication Critical patent/GB707903A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/82—Purification; Separation; Stabilisation; Use of additives
    • C07C209/86—Separation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/08—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

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

Abstract

The D- and L-threo-isomers of 1-p-nitrophenyl - 2 - aminopropane - 1,3 - diol are separated into their optically active D-(-)- and L-(+)-isomers by reacting mixtures of the said amino-diols with L-(+)-glutamic acid, separating the resulting acid addition salts of the D-and L-isomers by fractional crystallization from an aqueous or anhydrous organic solvent, and separately neutralizing the acid addition salts of the separated D- and L-isomers to obtain the corresponding separate D- and L-optical isomers of the free base of the amino diol. Aliphatic alcohols of not more than 5 carbon atoms are suitable solvents. Ammonium hydroxide and dilute aqueous sodium or potassium hydroxide are specified for neutralisation. In three examples a racemic mixture of the DL-threo-amino-diol is resolved using ethanol or industrial methylated spirit as solvent the neutralisation being effected to pH 9 to 10 with dilute ammonium hydroxide. Specification 652,275 is referred to.
GB11057/51A 1951-05-10 1951-05-10 Improvements in or relating to the resolution of isomeric mixtures of 1-p-nitrophenyl-2-aminopropane-1,3-diol Expired GB707903A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB11057/51A GB707903A (en) 1951-05-10 1951-05-10 Improvements in or relating to the resolution of isomeric mixtures of 1-p-nitrophenyl-2-aminopropane-1,3-diol

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB11057/51A GB707903A (en) 1951-05-10 1951-05-10 Improvements in or relating to the resolution of isomeric mixtures of 1-p-nitrophenyl-2-aminopropane-1,3-diol

Publications (1)

Publication Number Publication Date
GB707903A true GB707903A (en) 1954-04-28

Family

ID=9979210

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11057/51A Expired GB707903A (en) 1951-05-10 1951-05-10 Improvements in or relating to the resolution of isomeric mixtures of 1-p-nitrophenyl-2-aminopropane-1,3-diol

Country Status (1)

Country Link
GB (1) GB707903A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2766286A (en) * 1953-07-15 1956-10-09 Lepetit Spa Process for the resolution of racemic threo-1-phenyl-2-amino-1. 3-propanediol
US2921959A (en) * 1954-05-20 1960-01-19 Roussel Uclaf Process of resolving dl-serine
US2991307A (en) * 1954-12-14 1961-07-04 Roussel Uclaf Process of resolving nu, nu-dibenzyl-dl-alpha-amino acids and products
US3056799A (en) * 1959-07-20 1962-10-02 Sterling Drug Inc Processes and intermediate products
US3682925A (en) * 1969-01-30 1972-08-08 Hoffmann La Roche ({31 )-di-o-isopropylidene-2-keto-l-gulonates
US3855227A (en) * 1972-05-08 1974-12-17 C Hollander ({31 )-di-o-isopropylidene-2-keto-l-gulonates
WO2006002972A1 (en) * 2004-07-05 2006-01-12 Sandoz Ag Process for the preparation of gabapentin

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2766286A (en) * 1953-07-15 1956-10-09 Lepetit Spa Process for the resolution of racemic threo-1-phenyl-2-amino-1. 3-propanediol
US2921959A (en) * 1954-05-20 1960-01-19 Roussel Uclaf Process of resolving dl-serine
US2991307A (en) * 1954-12-14 1961-07-04 Roussel Uclaf Process of resolving nu, nu-dibenzyl-dl-alpha-amino acids and products
US3056799A (en) * 1959-07-20 1962-10-02 Sterling Drug Inc Processes and intermediate products
US3682925A (en) * 1969-01-30 1972-08-08 Hoffmann La Roche ({31 )-di-o-isopropylidene-2-keto-l-gulonates
US3855227A (en) * 1972-05-08 1974-12-17 C Hollander ({31 )-di-o-isopropylidene-2-keto-l-gulonates
WO2006002972A1 (en) * 2004-07-05 2006-01-12 Sandoz Ag Process for the preparation of gabapentin

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