GB1426186A - Process for the resolution of d,1 2- 6-methoxy-2-naphthyl- propionic acid - Google Patents

Process for the resolution of d,1 2- 6-methoxy-2-naphthyl- propionic acid

Info

Publication number
GB1426186A
GB1426186A GB3026873A GB3026873A GB1426186A GB 1426186 A GB1426186 A GB 1426186A GB 3026873 A GB3026873 A GB 3026873A GB 3026873 A GB3026873 A GB 3026873A GB 1426186 A GB1426186 A GB 1426186A
Authority
GB
United Kingdom
Prior art keywords
naphthyl
methoxy
propionic acid
salt
water
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
GB3026873A
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 Palo Alto LLC
Original Assignee
Roche Palo Alto LLC
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 Palo Alto LLC filed Critical Roche Palo Alto LLC
Publication of GB1426186A publication Critical patent/GB1426186A/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
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1426186 Resolution of d-, l- 2 - (6 - methoxy - 2 - naphthyl) - propionic acid SYNTEX CORP 26 June 1973 [10 Aug 1972] 30268/73 Heading C2C A process for separating d-2-(6-methoxy-2- naphthyl) propionic acid from a mixture of d- and l-2-(6-methoxy-2-naphthyl) propionic acid comprises providing a heated two-phased system having water as an aqueous phase and a water-immiscible, inert non-polar organic solvent as an organic phase, a salt of d-2-(6-methoxy-2-naphthyl) propionic acid and a salt of l-2- (6-methoxy-2-naphthyl) propionic acid being in said two-phase system, and a salt of dehydroabietylamine which is soluble in said organic phase but is essentially insoluble in said aqueous phase; holding said two-phase system at a temperature from 40‹ to 100‹ C. Vo promote the formation of the dehydroabietylamine salt of l-2-(6-methoxy-2-naphthyl) propionic acid; crystallizing said dehydroabietylamine salt of l - 2 - (6 - methoxy - 2 - naphthyl) propionic acid; separating said crystallized salt from said two-phase system to thereby provide a mother liquor which is enriched in the water soluble salt of d-2-(6-methoxy-2-naphthyl) propionic acid; separating said aqueous phase from said organic phase; and salting out a salt of d-2-(6-methoxy-2-naphthyl) propionic acid by adding to said aqueous phase an inorganic salt which is more soluble in said aqueous phase than in said water-soluble salt of d-2-(6-methoxy-2-naphthyl) propionic acid and crystallizing the least water-soluble salt of d-2-(6-methoxy-2-naphthyl) propionic acid from said aqueous phase and optionally dissolving said crystalline salt of d - 2 - (6 - methoxy - 2 - naphthyl) propionic acid in a solvent, acidifying said solution with a mineral acid to yield d-2-(6-methoxy- 2-naphthyl) propionic acid, and crystallizing substantially pure d-2-(6-methoxy-2-naphthyl) propionic acid therefrom. Examples of the water-immiscible, inert organic solvents are toluene, benzene and xylene.
GB3026873A 1972-08-10 1973-06-26 Process for the resolution of d,1 2- 6-methoxy-2-naphthyl- propionic acid Expired GB1426186A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US27932972A 1972-08-10 1972-08-10

Publications (1)

Publication Number Publication Date
GB1426186A true GB1426186A (en) 1976-02-25

Family

ID=23068502

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3026873A Expired GB1426186A (en) 1972-08-10 1973-06-26 Process for the resolution of d,1 2- 6-methoxy-2-naphthyl- propionic acid

Country Status (11)

Country Link
JP (1) JPS5339421B2 (en)
AU (1) AU474834B2 (en)
BE (1) BE803394A (en)
CA (1) CA1000731A (en)
CH (1) CH581602A5 (en)
ES (1) ES417692A1 (en)
FR (1) FR2195438B1 (en)
GB (1) GB1426186A (en)
IL (1) IL42485A (en)
NL (1) NL7310838A (en)
SE (1) SE406320B (en)

Also Published As

Publication number Publication date
AU474834B2 (en) 1976-08-05
FR2195438B1 (en) 1976-10-22
IL42485A (en) 1977-05-31
NL7310838A (en) 1974-02-12
JPS5339421B2 (en) 1978-10-21
ES417692A1 (en) 1976-05-16
IL42485A0 (en) 1973-08-29
DE2339765A1 (en) 1974-02-28
AU5751173A (en) 1975-01-09
SE406320B (en) 1979-02-05
CH581602A5 (en) 1976-11-15
JPS4945047A (en) 1974-04-27
CA1000731A (en) 1976-11-30
DE2339765B2 (en) 1976-04-29
FR2195438A1 (en) 1974-03-08
BE803394A (en) 1974-02-11

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee