Sodium Hydroxide → 5-Deazaaminopterin

HRID 370523

Reaktionsgleichung

Reaktionsgleichung von HRID 370523
[NH2:1][C:2]1[N:3]=[C:4]([NH2:36])[C:5]2[CH:11]=[C:10]([CH2:12][NH:13][C:14]3[CH:35]=[CH:34][C:17]([C:18]([NH:20][C@H:21]([C:29]([O:31]CC)=[O:30])[CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])=[O:19])=[CH:16][CH:15]=3)[CH:9]=[N:8][C:6]=2[N:7]=1.[OH-].[Na+]>CS(C)=O>[NH2:1][C:2]1[N:3]=[C:4]([NH2:36])[C:5]2[CH:11]=[C:10]([CH2:12][NH:13][C:14]3[CH:35]=[CH:34][C:17]([C:18]([NH:20][C@H:21]([C:29]([OH:31])=[O:30])[CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[O:19])=[CH:16][CH:15]=3)[CH:9]=[N:8][C:6]=2[N:7]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 12908481Diethyl N-[4-[(2,4-diaminopyrido[2,3-d]pyrimidin-6-yl)methylamino]benzoyl]-L-glutamate

Produkt 1

HCID 972725-Deazaaminopterin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of the product obtained in Example 3, VII (R=H; R1 =C2H5) (359 mg, 0.724 mmol) in dimethyl sulfoxide (10 ml) under N2 was treated with 1N NaOH (1.81 ml, 1.81 mmol), stirred in a stoppered flask under N2 for 6 hours, and evaporated to dryness in vacuo at <30° C. A solution of the residue in water (18 ml) was filtered and acidified to pH 3.6 with 1N HCl. The precipitate was collected by filtration, washed with water at pH 3.6 and dried in vacuo (P2O5); yield 297 mg (87%), mp indefinite (softens above 200° C.); mass spectrum, m/e 440 (M+1)+ ; λmax nm (ε×10-3): 0.1N HCl-218 (40.5), 280 sh (16.9), 300 (18.8); pH 7-218 (38.5), 245 (19.2), 280 (23.9), 296 sh (22.7); 0.1N NaOH-248 (22.0), 280 (24.4), 296 sh (22.7), 345 (7.75); 1H-NMR (DMSO-d6, 6% w/v), δ2.00 m (CH2CH2CO), 2.29 t (CH2CO), 4.36 m (CHN, CH2N), 6.66 d, 7.68 d (C6H4), 7.41 (NH2), 8.04 m (NH2, NH, CO2H), 8.52 d, 8.70 d (5-CH, 7-CH).

Aufarbeitung

  1. customevaporated to dryness in vacuo at <30° C
  2. filtrationA solution of the residue in water (18 ml) was filtered
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water at pH 3.6
  5. dry with materialdried in vacuo (P2O5)
  6. customyield 297 mg (87%), mp indefinite (softens above 200° C.)
  7. wait1H-NMR (DMSO-d6, 6% w/v), δ2.00 m (CH2CH2CO), 2.29 t (CH2CO), 4.36 m (CHN, CH2N), 6.66 d, 7.68 d
  8. custom(C6H4), 7.41 (NH2), 8.04 m (NH2, NH, CO2H), 8.52 d, 8.70 d (5-CH, 7-CH)

Quellen und Nachweise

ORD-Eintrag
ord-cdd919faf88a45c29574ced7401a7064
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04526964

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