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US3725465A Expired / Lapsed US ⏱️ 0.0 years remaining

Preparation of l-3,4-dihydroxy-phenyl-alanine

Assignee: Roche Diagnostics GmbH
•
Filing: 1971-08-03
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Granted: 1973-04-03
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Expires: 1991-08-03
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Abstract

Abstract To an aqueous solution of D,L-N-benzoyl-3,4-dimethoxy-phenylalanine there is added at least one amine selected from the group consisting of D(-)-threo-1-m-nitrophenyl-2-amino-propanediol-1,3, D(-)-threo-1-p-nitrophenyl-2-amino-propanediol-1,3 and D(-)threo-1-phenyl-2-amino-propanediol-1,3 selectively to precipitate the amine salt of the L-stereoisomer which is separated, dissolved and acidified to precipitate the free L-stereoisomer which is saponified to L-3,4-dihydroxy-phenyl-alanine. The mother liquor from the initial precipitation containing the amine salt of the D-stereoisomer and some L-stereoisomer is acidified to precipitate the free stereoisomers, leaving the amine in the acidified solution. The precipitated free stereoisomers are racemized and recycled for recovery of additional L-stereoisomer. The acidified solution of amine is rendered alkaline and steps are taken to regenerate and recycle the free amine.

Inventors

  • 👤 G Stoeck
  • 👤 W Gradel
  • 👤 H Budka
  • 👤 F Topfmeier

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 08:35
CPC Classifications
C; C07; C07C; C07C229/00; C07C229/02; C07C229/34; C07C229/36; C07C235/00; C07C235/70; C07C235/84; C07C231/00; C07C231/02; C07B; C07B2200/00; C07B2200/07

Claims Analysis

Total Claims: 4
Claim 1
Independent Claim 41 words
Process according to claim 1, wherein there is also added to said solution up to about 0.5 mole of sodium hydroxide per mole of D,L-N-benzoyl-3,4-dimethoxy-phenylalanine, the total of amine plus sodium hydroxide being substantially about 1 mole per mole of D,L-N-benzoyl-3,4-dimethoxy-phenyl-alanine.
Claim 2
Dependent Claim 10 words
Process according to claim 1, wherein said amine is D(-)-threo-1-m-nitrophenyl-2-amino-propanediol-1,3.
Claim 3
Dependent Claim 18 words
The L-N-benzoyl-3,4-dimethoxy-phenyl-alanine salt of at least one amine selected from the group consisting of D-(-)-threo-1-m-nitrophenyl-2-amino-propanediol-1,3, D-(-)-threo-1-p-nitrophenyl-2-amino-propanediol-1,3, and D(-)-threo-1-phenyl-2-amino-propanediol-1,3.
Claim 4
Dependent Claim 11 words
A salt according to claim 4, wherein said amine is D(-)-threo-1-m-nitrophenyl-2-amino-propanediol-1,3.

References Cited (Backward Citations)

US3590077A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1976-04-02 1976-10-02 1977-04-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1980-04-02 1980-10-02 1981-04-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1984-04-02 1984-10-02 1985-04-03 $7700.00 Window Closed / Lapsed

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