GB695741A - Optically active -a-phenyl-serine compounds and process for the manufacture thereof - Google Patents

Optically active -a-phenyl-serine compounds and process for the manufacture thereof

Info

Publication number
GB695741A
GB695741A GB8635/51A GB863551A GB695741A GB 695741 A GB695741 A GB 695741A GB 8635/51 A GB8635/51 A GB 8635/51A GB 863551 A GB863551 A GB 863551A GB 695741 A GB695741 A GB 695741A
Authority
GB
United Kingdom
Prior art keywords
threo
phenylserine
quinine
salt
acyl
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
GB8635/51A
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.)
Roche Products Ltd
Original Assignee
Roche Products 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 Roche Products Ltd filed Critical Roche Products Ltd
Publication of GB695741A publication Critical patent/GB695741A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C229/34—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 containing six-membered aromatic rings
    • C07C229/36—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 containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
    • 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
    • C07C229/22—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 the carbon skeleton being further substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • 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 invention comprises L-threo-b -phenylserine and its N-acyl derivatives, and salts thereof, including salts of the N-acyl compounds with optically active bases, and the manufacture of these compounds and of aliphatic alcohol esters of L-threo-b -phenylserine by acylating DL-threo-b -phenylserine or an alkyl ester thereof at the amino group, hydrolysing the ester group if present, reacting the resulting DL-threo-N-acyl-b -phenylserine or an alkali metal salt thereof with an optically active base or a salt thereof respectively, separating from the mixture of diastereoisomeric salts the L-threo-N-acyl-b -phenylserine salt, if desired decomposing the latter, further, if desired, hydrolysing off the N-acyl group, and finally, if desired, esterifying the L-threo-b -phenylserine with an aliphatic alcohol. Preferably acylation is effected with acetic anhydride, quinine is used as the optically active base, p and the separation of the diastereoisomers is effected by fractional crystallization from water, from which the desired isomer separates first. An advantageous procedure consists in reacting the sodium salt of DL-threo-N-acetyl-b -phenylserine with only half a molecular proportion of quinine hydrochloride in warm aqueous solution, whereby, on cooling, the quinine salt of the L-form crystallizes out and the sodium salt of the D-form remains in solution. In examples: (1) DL-threo-b -phenylserine is esterified by suspending it in ethanol and passing in hydrogen chloride, the ester is liberated from the resulting hydrochloride by the action of ammonia and acetylated with acetic anhydride in glacial acetic acid, the N-acetyl ester is hydrolyzed with dilute caustic soda followed by treatment with hydrochloric acid, the DL-threo-N-acetyl-b -phenylserine is reacted with quinine in hot water and the quinine salt of the L-threo acid is crystallized, decomposed with aqueous alcoholic caustic soda and hydrolysed with hydrochloric acid; (2) DL-threo-b -phenylserine is acetylated with acetic anhydride in aqueous caustic soda, the sodium salt of the N-acetyl compound is reacted with half a molecular proportion of quinine hydrochloride, and the quinine salt of the L-threo acid is crystallized, decomposed with aqueous caustic soda in the presence of chloroform and hydrolysed with hydrochloric acid; (3) L-threo-b -phenylserine is esterified by treatment with ethanolic hydrochloric acid, the ester being liberated from its hydrochloride by the action of ammonia.
GB8635/51A 1950-04-14 1951-04-13 Optically active -a-phenyl-serine compounds and process for the manufacture thereof Expired GB695741A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH695741X 1950-04-14

Publications (1)

Publication Number Publication Date
GB695741A true GB695741A (en) 1953-08-19

Family

ID=4529620

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8635/51A Expired GB695741A (en) 1950-04-14 1951-04-13 Optically active -a-phenyl-serine compounds and process for the manufacture thereof

Country Status (1)

Country Link
GB (1) GB695741A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5874613A (en) * 1994-03-03 1999-02-23 Daicel Chemical Industries, Ltd. 3-(3-chlorophenyl) serine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5874613A (en) * 1994-03-03 1999-02-23 Daicel Chemical Industries, Ltd. 3-(3-chlorophenyl) serine

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