GB773174A - Resolution of d,l-pantolactone - Google Patents

Resolution of d,l-pantolactone

Info

Publication number
GB773174A
GB773174A GB24373/55A GB2437355A GB773174A GB 773174 A GB773174 A GB 773174A GB 24373/55 A GB24373/55 A GB 24373/55A GB 2437355 A GB2437355 A GB 2437355A GB 773174 A GB773174 A GB 773174A
Authority
GB
United Kingdom
Prior art keywords
dimethyl
pantolactone
hydroxy
resolution
butyrolactone
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
GB24373/55A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of GB773174A publication Critical patent/GB773174A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • 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
    • C07C233/16—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 singly-bound oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention comprises a compound having the formula <FORM:0773174/IV(b)/1> and a process for the resolution of a mixture of D(-)a - hydroxy - b ,b - dimethyl - g - butyro - lactone and L(+)a - hydroxy - b ,b - dimethyl - g -butyrolactone which comprises reacting the mixture with D(-) galactamine to produce the diastereoisomers (-) - N - D - dulcityl - L - (a ,g - dihydroxy-b ,b -dimethylbutyramide) and (+)-N - D - dulcityl - D - (a ,g - dihydroxy - b ,b - dimethyl-butyramide), separating the diastereoisomers from each other, e.g. by countercurrent extraction, chromatography, or fractional crystallization, and hydrolysing the separated compounds. The resulting L(+)a -hydroxy-b ,b -dimethyl-g -butyrolactone may be racemized to produce an additional quantity of D(-)a -hydroxy - b ,b - dimethyl - g - butyrolactone. The (-) pantolactone and (+) pantolactone may be reacted with D(-) galactamine by fusing together or by heating in an inert organic solvent. Examples describe the resolution of D,L-pantolactone, and the preparation of (+) dulcitylpantamide and (-) dulcitylpantamide m.p. 122-3 DEG C. and its polymorph m.p. 162-5 DEG C.
GB24373/55A 1954-09-09 1955-08-24 Resolution of d,l-pantolactone Expired GB773174A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US773174XA 1954-09-09 1954-09-09

Publications (1)

Publication Number Publication Date
GB773174A true GB773174A (en) 1957-04-24

Family

ID=22137360

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24373/55A Expired GB773174A (en) 1954-09-09 1955-08-24 Resolution of d,l-pantolactone

Country Status (1)

Country Link
GB (1) GB773174A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001049671A1 (en) * 1999-12-29 2001-07-12 Oxis Isle Of Man, Limited Methods for resolving racemic mixtures of 5-substituted 4-hydroxy-2-furanones

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001049671A1 (en) * 1999-12-29 2001-07-12 Oxis Isle Of Man, Limited Methods for resolving racemic mixtures of 5-substituted 4-hydroxy-2-furanones
US6613919B2 (en) 1999-12-29 2003-09-02 Oxis Isle Of Man Method for resolving racemic mixtures of 5-substituted 4-hydroxy-2-furanones

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