Ethanol → 5,11-Methenyltetrahydrohomofolate

HRID 1638599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1638599
C([NH:4][C:5]1[NH:6][C:7](=[O:39])[C:8]([CH2:15][CH2:16][CH2:17][NH:18][C:19]2[CH:38]=[CH:37][C:22]([C:23]([NH:25][C@H:26]([C:33]([O:35]C)=[O:34])[CH2:27][CH2:28][C:29]([O:31]C)=[O:30])=[O:24])=[CH:21][CH:20]=2)=[C:9]([NH:11]C(=O)C)[N:10]=1)(=O)C.C(O)C.[OH-].[Na+].N1C=CC=CC=1>O.C(O)CCC>[NH2:4][C:5]1[NH:6][C:7](=[O:39])[C:8]([CH2:15][CH2:16][CH2:17][NH:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([NH:25][C@H:26]([C:33]([OH:35])=[O:34])[CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:24])=[CH:37][CH:38]=2)=[C:9]([NH2:11])[N:10]=1

Komponenten

7

Edukt 4

HCID 702EthanolHCID 1049PyridineHCID 14798Sodium HydroxideHCID 135990644HCID 135990644, Verbindung

Produkt 1

HCID 1354075895,11-Methenyltetrahydrohomofolate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A stirred solution of 1.60 g (2.89 mmol) of dimethyl N-[4-[3-(2,4-bis(acetamido)-1,6-dihydro-6-oxo-5-pyrimidinyl)propylamino]benzoyl]-L-glutamate, 50 ml of ethanol and 100 ml of 1 N sodium hydroxide was heated at 50°-60° for 20 hours. The cooled reaction was spin evaporated in vacuo to 50 ml, cooled, and neutralized to pH 5-6 with concentrated hydrochloric acid. The resultant white precipitate was collected, washed with water, diethylether and dried; yield, 0.86 g (66%) mp (sinter 170°) 198°-202° (eff). Recrystallization from methanol gave the analytical sample; yield, 0.33 g (39%), mp (forms hard foam 180°) 200° (eff); TLC (pyridine:BuOH:H2O/1:1:1); NMR (DMSO-D6)δ8.07 (d, 1H, ArCONH), 7.65 (d, 2H, ArH), 6.54 (d, 2H, ArH), 6.22 (br s, 1H, CH2NH), 5.94 (s, 2H, NH2), 5.75 (s, 2H, NH2), 4.34 (m, 1H, CHCO2H), 3.03 (m, 2H, CH2NHAr), 2.30 (m, 4H, pyrimidine-CH2 and CH2CO2H), 2.03 (m, 2H, CHCH2), 1.58 (m, 2H, CH2CH2CH2).

Aufarbeitung

  1. customThe cooled reaction
  2. customevaporated in vacuo to 50 ml
  3. temperaturecooled
  4. customThe resultant white precipitate was collected
  5. washwashed with water, diethylether
  6. customdried
  7. customyield
  8. custom0.86 g (66%) mp (sinter 170°) 198°-202° (eff)
  9. customRecrystallization from methanol
  10. customgave the analytical sample
  11. customyield
  12. custom0.33 g (39%), mp (forms hard foam 180°) 200° (eff)

Quellen und Nachweise

ORD-Eintrag
ord-05004dda8a084946b8973bb297035f26
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04880812

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