Methotrexate → HCID 178432404, Verbindung

HRID 905098

Reaktionsgleichung

Reaktionsgleichung von HRID 905098
CN(C1C=[CH:18][C:19]([C:22](N[C@H](C(O)=O)CCC(O)=O)=[O:23])=CC=1)CC1C=NC2N=C(N)N=C(N)C=2N=1.Cl.[NH2:35][C:36]1[N:41]=[C:40]([NH2:42])[N:39]=[C:38]([NH2:43])[C:37]=1[NH2:44].OC(O)C(=O)C>O>[NH2:42][C:40]1[N:41]=[C:36]([NH2:35])[C:37]2[C:38](=[N:43][C:19]([CH3:18])=[C:22]([OH:23])[N:44]=2)[N:39]=1

Komponenten

5

Edukt 3

HCID 126941MethotrexateHCID 131809821,1-Dihydroxypropan-2-oneHCID 204773462,4,5,6-Tetraaminopyrimidine hydrochloride

Produkt 1

HCID 178432404HCID 178432404, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

The well-known Ellard process is exemplified by U.S. Pat. No. 4,080,325 Ellard and claim 1 of the patent sets out the steps for preparing methotrexate as follows: (a) reacting tetraaminopyrimidinehydrochloride with dihydroxyacetone in the presence of air and water and at a pH in the range of 5.5±0.2 to give 2,4-diamino-6-hydroxy-methylpteridine; (b) converting the 2,4-diamino-6-hydroxy-methylpteridine to the hydrobromide salt, namely, 2,4-diamino-6-hydroxymethylpteridine hydrobromide salt; (c) reacting the 2,4-diamino-6-hydroxymethylpteridine hydrobromide salt with triphenyldibromophosphorane to give 2,4-bis(triphenylphosphazine)-6-bromomethylpteridine hydrobromide; (d) reacting the 2,4-bis(triphenylphosphazino)-6-bromomethylpteridine hydrobromide with ethyl N-(p-methylamino)benzylglutamate to give the phosphazino derivative of methotrexate ester; (e) hydrolyzing the phosphazino derivative of methotrexate ester to give triphenylphosphine oxide and methotrexate ester; and (f) hydrolyzing the methotrexate ester to give methotrexate.

Quellen und Nachweise

ORD-Eintrag
ord-a2a198a517b241ec97f299a38a94d584
Quelldatensatz
uspto-grants-1983_12
Patentnummer
US04421913

Verknüpfte Notizen

Wird geladen…