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Sodium Hydroxide → (2S)-2-[[4-[(2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid

HRID 1681705
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1681705
C(O)(=O)CC[C@H](NC(C1C=CC(NCC2N=C3C(N=C(NC3=O)N)=NC=2)=CC=1)=O)C(O)=O.BrC(CBr)C=O.NC1N=C(N)C(N)=C(O)N=1.NC1C=CC(CN[C@H](C(O)=O)CCC(O)=O)=CC=1.[OH-].[Na+].C([O-])(=O)CC[C@H](NC(C1C=CC(NCC2N=C3C(N=C(NC3=O)N)=NC=2)=CC=1)=O)C(O)=O.[Na+].[CH2:102]1[NH:107][C:106]2[NH:108][C:109]([NH2:113])=[N:110][C:111](=[O:112])[C:105]=2[N:104]([CH:114]=[O:115])[CH:103]1[CH2:116][NH:117][C:118]1[CH:123]=[CH:122][C:121]([C:124]([NH:126][C@H:127]([C:133]([O-:135])=[O:134])[CH2:128][CH2:129][C:130]([O-:132])=[O:131])=[O:125])=[CH:120][CH:119]=1.[Ca+2]>O.C(O)=O.[Pt]=O.O1CCOCC1>[CH:122]1[C:121]([C:124]([NH:126][C@H:127]([C:133]([OH:135])=[O:134])[CH2:128][CH2:129][C:130]([OH:132])=[O:131])=[O:125])=[CH:120][CH:119]=[C:118]([NH:117][CH2:116][CH:103]2[N:104]([CH:114]=[O:115])[C:105]3[C:111]([N:110]=[C:109]([NH2:113])[NH:108][C:106]=3[NH:107][CH2:102]2)=[O:112])[CH:123]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

12

Edukt 7

HCID 14798Sodium HydroxideHCID 922162,3-DibromopropanalHCID 53968688p-Aminobenzylglutamic acidHCID 135398658Folic Acid2×HCID 136359212Sodium folateHCID 178508811HCID 178508811, Verbindung
HCID 178508911
calcium (2S)-2-[[4-[(2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioate

Produkt 1

HCID 178508910(2S)-2-[[4-[(2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 82844Platinum oxide (PtO)KatalysatorHCID 284Formic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Folic acid and its salts can be prepared by any convenient method, for example 2,3-dibromopropionaldehyde, dissolved in a water miscible organic solvent (alcohol, dioxane), is added to a solution of equal molecular quantities of 2,4,5-triamino-6-hydroxypyrimidine and p-aminobenzylglutamic acid, maintaining a pH of about 4 by the controlled addition of alkali as the reaction progresses. If sodium hydroxide is used as the alkali, sodium folate is obtained. To make calcium leucovorin, folic acid is, for example simultaneously hydrogenated and formulated in 90 to 100% formic acid under the influence of platinum oxide catalyst to yield leucovorin. Conversion to the calcium salt may be accomplished by dissolving the leucovorin in sodium hydroxide solution, treating the calcium chloride, and precipitating with ethanol.

Aufarbeitung

  1. temperaturemaintaining a pH of about 4
  2. additionby the controlled addition of
  3. customalkali as the reaction progresses
  4. customis obtained

Quellen und Nachweise

ORD-Eintrag
ord-fe8b3ad1ad6d44d1a916cb6ae7124555
Quelldatensatz
uspto-grants-1992_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05173488

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