GB1321161A - Process for the manufacture of phenylalanine derivatives - Google Patents

Process for the manufacture of phenylalanine derivatives

Info

Publication number
GB1321161A
GB1321161A GB5033371A GB5033371A GB1321161A GB 1321161 A GB1321161 A GB 1321161A GB 5033371 A GB5033371 A GB 5033371A GB 5033371 A GB5033371 A GB 5033371A GB 1321161 A GB1321161 A GB 1321161A
Authority
GB
United Kingdom
Prior art keywords
alkyl
boric acid
salt
phenyl
compounds
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
GB5033371A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1321161A publication Critical patent/GB1321161A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/02—Boron compounds
    • C07F5/04—Esters of boric acids
    • 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
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

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

Abstract

1321161 Preparation of N-acyl dihydroxyphenylalanine derivatives and boric acid complexes thereof F HOFFMANN-LA ROCHE & CO AG 29 Oct 1971 [30 Oct 1970] 50333/71 Headings C2B and C2C Solutions of boric acid complexes of compounds of the general formula or salts thereof, where R 1 -R 3 are H or alkyl or two of the symbols together are alkylene, A is H or -COR 4 where R 4 is -OH; alkoxy which may be substituted by alkenyl, alkynyl or phenyl; or amino which may be alkyl-substituted, R 5 -R 7 are H, halogen, alkyl, alkoxy, nitro or dialkylamino, R 8 is H, alkyl, phenyl or phenylalkyl and R 9 is alkyl, phenylalkyl, phenyl or phenylalkoxy and where (a) the aliphatic groups, or portions of, R 1 -R 9 are C 1-18 , (b) the phenolic OH groups are ortho to each other, (c) when R 1 is H, A is -COR 4 and R 9 is alkyl, the N atom can (minus R 7 and R 8 ) be joined to the 2- or 6-carbon of the phenyl ring and (d) when R 1 -R 3 and R 5 -R 7 are H, A is carboxy and R 9 is phenylalkoxy, the compounds are in DL- or D-form, the phenolic OH groups being esterified with boric acid, are prepared by treating a compound of formula or a salt thereof, with boric acid or a borate at a pH of at least 7 and reacting the complex obtained with an agent furnishing a -COR 9 group while maintaining the pH of at least 7. The compounds of general Formula (I) are prepared from the solutions of the boric acid complexes by subjecting them to acidic hydrolysis and, if desired, (a) esterifying an acid of Formula I obtained or a salt thereof, (b) subjecting an ester of Formula I obtained or a salt thereof to a mild basic hydrolysis or to treatment with NH 3 , an alkylamine or a dialkylamine or (c) converting a product obtained into a salt. In the Examples the following compounds, and also solutions containing the corresponding boric acid complex starting material, are prepared: N - acetyl - L - dopa (where L - dopa is L - 3 - (3,4 - dihydroxyphenyl) - alanine); N - acetyl - DL - α - methyldopa; N-benzoyl- L - dopa; N - benzyloxycarbonyldopamine; N - acetyl - L - cyclodopa which is subsequently converted into the methyl ester, and N-acetyldopamine.
GB5033371A 1970-10-30 1971-10-29 Process for the manufacture of phenylalanine derivatives Expired GB1321161A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1604670A CH545280A (en) 1970-10-30 1970-10-30 Process for the preparation of phenylalanine derivatives

Publications (1)

Publication Number Publication Date
GB1321161A true GB1321161A (en) 1973-06-20

Family

ID=4414042

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5033371A Expired GB1321161A (en) 1970-10-30 1971-10-29 Process for the manufacture of phenylalanine derivatives

Country Status (7)

Country Link
BE (1) BE774676A (en)
CA (1) CA921929A (en)
CH (1) CH545280A (en)
DE (1) DE2153823A1 (en)
FR (1) FR2111951B1 (en)
GB (1) GB1321161A (en)
NL (1) NL7113514A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987004154A1 (en) * 1986-01-03 1987-07-16 The University Of Melbourne Melphalan derivatives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU195424B (en) * 1986-01-21 1988-05-30 Egyt Gyogyszervegyeszeti Gyar Process for the production of medical solutions containing l-3,4-dihydroxi-phenil-alpha-methil-alanine

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987004154A1 (en) * 1986-01-03 1987-07-16 The University Of Melbourne Melphalan derivatives
US5075108A (en) * 1986-01-03 1991-12-24 Consolidated Pharmaceuticals, Limited Melphalan derivatives

Also Published As

Publication number Publication date
CH545280A (en) 1973-12-15
BE774676A (en) 1972-05-02
FR2111951A1 (en) 1972-06-09
DE2153823A1 (en) 1972-05-10
NL7113514A (en) 1972-05-03
CA921929A (en) 1973-02-27
FR2111951B1 (en) 1973-06-29

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees